Bridgewater College Digital Commons

Whitaker, Kiya

Philomathean 
Volume 3 MMXXIV: Where Our Dreams Take Us Article 46 
2-14-2024 
The Playground 
Kiya Whitaker 
Bridgewater College, kwhitaker@eagles.bridgewater.edu 
Follow this and additional works at: https://digitalcommons.bridgewater.edu/bc_philomathean 
Recommended Citation 
Whitaker, Kiya (2024) "The Playground," Philomathean: Vol. 3, Article 46. 
Available at: https://digitalcommons.bridgewater.edu/bc_philomathean/vol3/iss1/46 
This Fiction is brought to you for free and open access by the Journals and Campus Publications at BC Digital 
Commons. It has been accepted for inclusion in Philomathean by an authorized editor of BC Digital Commons. For 
more information, please contact rlowe@bridgewater.edu. 
The Playground
Kiya Whitaker
Bree and I seemed more like siblings than friends. It helped that I lived right next door to
her, and our bedroom windows sat across from each other. We’d communicate through them
before we had phones, sometimes shouting things or using whiteboards when we didn’t want to
get caught staying up past bedtime. During the summer, we had adventures around the yard or
down the street, often taking my dog Barnaby along with us in case of danger. In the summer
right before fifth grade, we found the playground.
It was the year of the heat wave, the one which made the whole town so damn stuffy. The
only thing you could do was lie on your bed with a thousand fans staring at you, or kneel before
the sprinklers in the yard, crawling to follow them as they turned. My parents never liked it when
we did that, once wishing to preserve the appearance of our yard before opting to preserve their
wallets when the sun became too difficult to combat. Most yards in the neighborhood went from
a vibrant green to a dull, brownish yellow. There weren’t any more flowers to attract bugs, which
I was grateful for, except for the lawn of Mr. Crowe. He had a sprawling garden of various
brightly colored fruits and flowers, and the sprinklers were always going. He lived alone in the
biggest house on our street, usually wearing a dark coat and wide-brimmed hat, despite the heat.
Most strikingly was his hair: long and white, even though he looked middle-aged at most.
I remember Bree and I taking Barnaby out for a walk, and we stopped at Mr. Crowe’s
place, hearing the soft patter of sprinkler water. I almost licked my lips at the sight of it too, and I
could tell Bree was thinking the same thing.
“C’mon, just this once,” she said to me.
Before I could protest, she dragged Barnaby’s leash into the opened gate of the yard. We
only danced in the mist for a couple of seconds when the creaky screen door of Mr. Crowe’s
house slammed open and made us go still.
“Can I help you?” he asked calmly.
“We’re just… trying to cool off,” I answered.
“Looking for something to do?”
Bree and I exchanged a look before smiling. He sat in the chair on his porch and stuck a
finger outward. I thought he was pointing for us to leave, but as I followed the direction of his
hand, I noticed the rugged trail in the woods. Most used it for forest walks, and sometimes my
parents took Barnaby out there. I don’t think Bree and I had ever been before that day.
“There’s an old park at the end of the road. Down the trail on the left. Far down.”
“A park?” Bree said.
He nodded. “I’m sure you’ll find something interesting down there.”
I assumed he wanted to get rid of us, so we didn’t accidentally ruin anything in the yard.
Bree and I didn’t question it, deciding to explore a new mystery. It wasn’t too long of a walk into
the woods, but the hanging branches and debris covering the walkway stalled us since I was
terrified of anything clinging to me. Most of all, ticks. When we finally left the woods, we came
to a chain link fence with a clearing on the other side. In that clearing was a trailer park, though it
seemed abandoned. Bree found an opening in the fence big enough for us to walk through, and
while she went inside, I didn’t move.
“Are you sure we should do this?” I asked her, clutching Barnaby’s leash so she couldn’t
grab it.
“Mr. Crowe wouldn’t send us anywhere dangerous, right?”
Right. For a kid, that made sense. Why would an adult tell me something wrong? Or send
me somewhere that might get me hurt? I didn’t know him well, but he was my neighbor, and my
parents spoke to him a couple of times, so it made sense to trust him. I followed Bree, and the
first thing we noticed were all the TVs lying around, of various ages, sizes, and models. Some
were in good condition –clean in-store condition– while others had seen better days. None of
them could turn on or had any wires for an outlet.
A lot of the trailers came with strange quirks. One had wooden planks boarding all the
windows and doors, and a terrible odor coming from it, like something rotten. We made sure to
avoid it. Another seemed to be a giant magnet, as coins, utensils, paper clips, and other metallic
objects stuck to its surface. The other trailers also leaned toward it slightly. There was one with
mangled road signs sticking in its dirt lawn and another that was upside down. At the center of
this place was a pit, maybe one or two feet deep. It had nothing of interest, so we didn’t bother it.
We decided to play around, making up ghost stories to explain this mysterious, new
“playground.” As the sun set, we took our questions back to Mr. Crowe, still sitting quietly on
his front porch.
“What is that place?” I asked him. “Is it safe?”
He looked at me with a smile, his eyes shielded by his hat. “Of course it is. I used to play
there all the time when I was a kid. Now, it’s yours. Go keep yourselves busy.”
And that was all we got from him. Maybe he knew just as much about the place as we
did, which was nothing, or he was keeping something from us. It didn’t stop us from going back,
or for Bree to convince me to go back with her. We decided to clear the trail that led there so we
could ride our bikes and save time. Then, we’d have adventures with Barnaby, sometimes
bringing things to use as props —an empty water gun, a plastic bucket, a frisbee that Bree threw
too far, landing out of sight. We searched every inch of the playground, following Barnaby’s
barks to the pit… which was empty. In frustration, Bree kicked some nearby stones into it, and it
seemed to grumble before thin, slimy, black tendrils, almost like worms, wrapped themselves
around the stones. They sunk the stones into the dirt, deepening the pit just a little. Bree and I
looked at each other with bewildered expressions, before hers shifted to awe.
She wanted to keep feeding it… whatever “it” was.
While she ran off in search of something else to toss in, I stared at the pit, scrunching my
face in disgust. Barnaby nudged against my leg while Bree returned with much larger stones.
When she threw them in, they landed with a soft squelch, as if the ground were damp. Then,
those worms returned and sucked the stones into the ground, once again expanding the pit. Bree
asked for my help, and together we attempted to drag one of the broken TVs in. But something
held it in place. There were wires after all, but they dug deep into the ground. While I held the
TV up, Bree stomped on the wire, disconnecting it from the TV. Strangely, the wire slid into the
dirt, almost like a worm…
It seemed all the TVs had something connecting them to the ground, but we opted to use
the broken ones. Over time, the worms in the pit were ready for whatever we tossed in, now
reaching out and dragging the TVs in before they could touch the ground. The sight of them
made me squirm. As I reached for another TV, Bree noticed the road signs and had us use those
instead. She thought that because they were bigger, it would satisfy the pit more. They were
farther from the pit and slid out of the ground easily.
Before, the worms took the TVs whole, but this time, they crumpled and bent the signs’
pole before sucking the entire thing in. I think we had made the pit about another foot or two
deep, maybe even a bit wider too, as the walls sloped a little more. More worms also gathered. I
couldn’t peel my eyes away as they stood taller, flailing violently. Some of the ground beneath
me slid away, and I almost fell in. Thankfully, Bree was able to catch me, and I stumbled away
from the pit with a loud cry. I guess the look on my face finally convinced her to call it quits. We
rode back home, and surprisingly, she suggested staying away from the playground.
But that was not our last visit.
It was the night of a fierce storm, and I woke up to Barnaby barking before he was cut
off. When I went downstairs to check on him, he was gone, and the front door lay wide open. On
the ground, leading out into the night, was a black trail of something wet. My stomach stirred,
and I rushed upstairs to tell my parents. They weren’t eager to head out into the pouring rain after
waking up in the middle of the night, but they went anyway. They told me to stay inside, but I
was convinced Barnaby’s disappearance had something to do with the pit. The worms. What else
could explain that trail?
I went to my window and knocked, waking up Bree, and used a whiteboard to tell her
what I was thinking. We threw on our raincoats and boots, grabbed some flashlights, and headed
for the woods. As I suspected, the black trail led back to the playground. I even noticed paw
prints stamped beside it: my worry turned to rage. The journey was slippery, but I didn’t care as
much when I fell into the mud a couple of times. When we arrived, something felt different. For
one, all the TVs were on, blaring static. The trailers rattled and shook with the wind and rain, and
a low rumble, or maybe more of a growl, could be felt through the ground. I knew where it came
from. The pit’s walls were covered in hundreds of dark worms, and the bottom was no longer
visible –now a void that slowly filled with rainwater. I shouted desperately for Barnaby, begging
the pit to set him free, cursing it, then promising to feed it whatever it wanted.
At that, all the TVs switched to an error screen, accompanied by the screeching tone that
always made me panic. While I jumped, Bree fell completely still, her eyes blank. She grabbed
me, ignoring my screams as her nails dug into my arms, and shoved me into the pit. I tried to
grab the dirt walls to stop my fall, but it wasn’t dirt, just rows and rows of worms. My grip
slipped and I plunged into the puddle at the bottom, falling back as the worms reached for me. I
couldn’t do a thing, so I screamed at Bree, but she only stood there and watched me.
Then I felt the worms on me… and I started to sink…
I kicked violently, my movements only hastening my descent into the pit. I could feel the
worms wrapping themselves around me, trying to dig into my skin. My screams worsened as I
clawed at myself, tearing out clumps of black mush and blood. By the time my legs were entirely
sunken in, I felt helpless, taking one last look up at Bree to see that she was gone. Instead, there
was someone else I couldn’t make out peering down at me. They held something bright and red
at their side: a torch that somehow burned despite the rain. The stranger descended into the pit
with me, landing without a grunt or cry, and swung the fire around. I started to feel a weight lift
from me as the ground around my legs and feet receded. The worms quickly crawled away,
burrowing into the dirt walls of the pit. As they all vanished, there was a low rumble again from
the underground, almost like a gurgle, but I wasted no time trying to climb back up. The stranger
gave me a boost and then scaled the walls after me, leaving the torch behind. The pit cowered
away from the fire, which continued to burn.
At the surface, I noticed the TVs were silent, their screens burst with shattered glass all
over the ground. Bree lay close by, and I had to be careful making my way over to her. Barnaby
stood at her side, licking her face, his fur soaked in rain but also covered in dark patches. I gave
him my raincoat and tended to Bree, slowly awakening. When she saw me, she started crying,
wrapping her arms around me, and apologizing between sobs. I cried with her, but the stranger
cut us off. The rain made it hard to see, but I recognized him.
“You kids alright?” Mr. Crowe said.
I nodded at him to say thanks, my throat raw. We returned home to see a police car on our
street and hurried to our parents. We told them everything, about the playground, the pit, the fall,
explaining the dirt and scratches all over me. The police agreed to check out the area, suggesting
we all head home for the night. Despite what we said, my mom focused on the fact that Mr.
Crowe put us in danger, even if it was unintentional, even though he saved us. She forbade Bree
and I from going near him or the playground again.
That night, I took a long, hot bath, scrubbing until my skin burned and checking every
inch of my body once I was dry. I still had scars from where the worms attempted to dig into me.
I checked my bed thoroughly for them before going to sleep, and that became a habit every night
until I moved out. I also often woke up from nightmares. I’m sure you know the kind– bursting
into fits of scratching and screaming. It was hard to go back to sleep as I could never shake off
the feeling that something was on me, crawling from my scars. Bree’s still weird about TV static
and even more panicky than I ever was whenever there’s a weather or amber alert.
When discussing everything later, Bree wasn’t sure what came over her when she pushed
me. She couldn’t control herself and felt paralyzed watching me struggle in the pit until Mr.
Crowe broke the TV screens. I could tell she felt awful about it and I didn’t have a hard time
forgiving her. My mother refused to tell me what the police updated them on, and Bree’s parents
did the same. I doubted there was anything to find, or that they believed us about any of it. Ghost
TVs, a living hole, evil worms? It sounded like a bunch of things kids imagine… or have
nightmares about. The police spent a lot of time asking us questions about Mr. Crowe, and
whether he ever said or did anything that made us uncomfortable. We told them the truth, and
even after that, our parents grilled us further. When our stories didn’t change, they switched to
educating us on the dangers of trusting strangers. I appreciate their concern, and I always
understood it, but if it weren’t for Mr. Crowe, I don’t think I’d still be alive. Or Bree.
She and I wanted to give him our thanks, but we rarely saw him outside his house or on
the porch after that, not even working in the garden. But it was always taken care of. There were
always bees nearby. School started soon after everything happened, and we tried our best to
move on, but so many questions remained. What was that place? Did Mr. Crowe know anything
more? Why did Barnaby disappear that night? (I still believe it was the worms) The thoughts ran
through my mind, but I could never find the courage to go back there. Neither could Bree. We
always assumed we’d go back one day, maybe not to find anything, but to conquer an old
childhood fear.
I never thought it’d be today.
It’s been over a decade since that summer. Bree and I don’t speak as much anymore, and
we moved from our childhood homes after high school. I never truly forgot what happened, on
account of the nightmares and the garish scars, but when I got word from my mother that Mr.
Crowe passed away, it all flooded back with stark clarity. She told me the house erupted in
flames one night and the police found Mr. Crowe still lying in bed. Through gossip, she
overheard that his body wasn’t as charred as it should’ve been, so the police were able to find
something thick and black stuck in his throat. My mind thought of the pit. The worms. The
autopsy reported more of this strange, “organic matter” lodged within his body, but the police
ruled the death as asphyxiation. They didn’t investigate further. Strangely enough, another
heatwave was taking place, and right before the night of his death, it stormed again.
I called Bree and we had this unspoken understanding about what to do next. An
understanding that led us to pack our bags and return to where we grew up– to that dreadful
place. We’ve armed ourselves with matches, lighters, hunting knives, and shovels, cutting a path
through the wooded trail and a doorway into the new fence. We ignore the new “private property,
no trespassing” sign, and when we get to the old playground, we realize we came overprepared.
Everything is gone. The trailers, the TVs, and the pit itself, filled in with new earth. We know
where it’s supposed to be, but we aren’t sure if it’s really gone. Bree and I stare at each other,
clutching our shovels tightly.
“Are you sure we should do this?” she asks me.
Kiya Whitaker studies Digital Media Arts at Bridgewater College


English

The Playground

Archival photograph from Bridgewater College Special Collectionshttps://digitalcommons.bridgewater.edu/track_and_field_photos/1035/thumbnail.jp

Bridgewater College

Bridgewater College, Photograph of Duane Harrison jumping, undated

Archival photograph from Bridgewater College Special Collectionshttps://digitalcommons.bridgewater.edu/track_and_field_photos/1032/thumbnail.jp

Bridgewater College, Photograph of Terry Lenny running, undated

Archival photograph from Bridgewater College Special Collectionshttps://digitalcommons.bridgewater.edu/bands_orchestra_photos/1026/thumbnail.jp

Bridgewater College, Photograph of a college band, undated

Beard, Casey

Philomathean 
Volume 3 MMXXIV: Where Our Dreams Take Us Article 3 
2-14-2024 
I Am 
Casey Beard 
Bridgewater College, cbeard3@eagles.bridgewater.edu 
Follow this and additional works at: https://digitalcommons.bridgewater.edu/bc_philomathean 
Recommended Citation 
Beard, Casey (2024) "I Am," Philomathean: Vol. 3, Article 3. 
Available at: https://digitalcommons.bridgewater.edu/bc_philomathean/vol3/iss1/3 
This Poetry is brought to you for free and open access by the Journals and Campus Publications at BC Digital 
Commons. It has been accepted for inclusion in Philomathean by an authorized editor of BC Digital Commons. For 
more information, please contact rlowe@bridgewater.edu. 
I Am
Casey Beard
I am soaring in the sky, high above the world in a bright red balloon, kept alive by flames alone. My best
friend stands beside me, laughing —
No.
I am laying on a beach, the warm sun beating down on my skin, staring out at the children as they run
into the ocean, howling and screaming with joy.
— No.
I’m a highschooler, driving to pick up my younger brothers after school because my parents can’t get
away from the office —
No.
I am a businesswoman, sitting at a bland desk with my name on it, in an uncomfortable suit, typing
away at something I’m pretending to understand —
I am a shard of ice, glistening within a crystal clear glacier. The sun shines down on me, and I know my
time is short. I know —
No.
I’m sitting in a room in the hospital for the fourth time in five months. My family is disappointed in me,
and I wonder why they still care.
I am swimming in a lake at the beginning of summer, feeling the cool water lap at my neck and
shoulders —
No.
I’m a wife, walking through the brightly lit grocery store and wondering if we will have enough to buy a
pack of cookies this month. I turn over the paper I’ve carefully budgeted everything out on, and —
I am a stone, sitting unturned in the forest. I don’t have many visitors, but the leaves always stop by and
say hello, even if —
No.
I am a son, bright-eyed and eager, ready to prove himself, ready to fight and die for his country. I’m about
to leave, and my mother cries, but my father nods at me. I feel something settle as I think I’ve earned his
respect.
— No.
I am happy, surrounded by friends and family. I am dying. I am happy. I am
Gone —
No —
I am soaring in the sky, high above the world in a bright red balloon, held up by flames alone. My best
friend stands beside me, laughing —
— and as I sleep, I know deep in my soul: I am home.
Casey Beard studies Psychology and Equine Studies at Bridgewater College


I Am

Bauer, Isabelle

Philomathean 
Volume 3 MMXXIV: Where Our Dreams Take Us Article 6 
2-14-2024 
Daydreams 
Isabelle Bauer 
Bridgewater College, ibauer@eagles.bridgewater.edu 
Follow this and additional works at: https://digitalcommons.bridgewater.edu/bc_philomathean 
Recommended Citation 
Bauer, Isabelle (2024) "Daydreams," Philomathean: Vol. 3, Article 6. 
Available at: https://digitalcommons.bridgewater.edu/bc_philomathean/vol3/iss1/6 
This Art is brought to you for free and open access by the Journals and Campus Publications at BC Digital 
Commons. It has been accepted for inclusion in Philomathean by an authorized editor of BC Digital Commons. For 
more information, please contact rlowe@bridgewater.edu. 
 Daydreams 
 Isabelle Bauer 
 Isabelle Bauer studies Digital Media Arts at Bridgewater College 


Daydreams

Quade, ShiLi

Philomathean 
Volume 3 MMXXIV: Where Our Dreams Take Us Article 19 
2-14-2024 
Bridgewater College 9/9/2023 
ShiLi Quade 
Bridgewater College, squade@eagles.bridgewater.edu 
Follow this and additional works at: https://digitalcommons.bridgewater.edu/bc_philomathean 
Recommended Citation 
Quade, ShiLi (2024) "Bridgewater College 9/9/2023," Philomathean: Vol. 3, Article 19. 
Available at: https://digitalcommons.bridgewater.edu/bc_philomathean/vol3/iss1/19 
This Multimedia is brought to you for free and open access by the Journals and Campus Publications at BC Digital 
Commons. It has been accepted for inclusion in Philomathean by an authorized editor of BC Digital Commons. For 
more information, please contact rlowe@bridgewater.edu. 
Bridgewater College 9/9/2023
ShiLi Quade
ShiLi Quade studies Digital Media Arts at Bridgewater College.


Bridgewater College 9/9/2023

Philomathean 
Volume 3 MMXXIV: Where Our Dreams Take Us Article 20 
2-14-2024 
Broken Dreams and Waking Truths 
Isabelle Bauer 
ibauer@eagles.bridgewater.edu 
Follow this and additional works at: https://digitalcommons.bridgewater.edu/bc_philomathean 
Recommended Citation 
Bauer, Isabelle (2024) "Broken Dreams and Waking Truths," Philomathean: Vol. 3, Article 20. 
Available at: https://digitalcommons.bridgewater.edu/bc_philomathean/vol3/iss1/20 
This Poetry is brought to you for free and open access by the Journals and Campus Publications at BC Digital 
Commons. It has been accepted for inclusion in Philomathean by an authorized editor of BC Digital Commons. For 
more information, please contact rlowe@bridgewater.edu. 
Broken Dreams and Waking Truths
Isabelle Bauer
Sometimes I still dream of you,
and it’s like nothing changed.
I feel your warmth,
and your smile too,
it makes me feel like it used to.
It feels so real,
that the fears start to creep in,
my stomach drops,
and my mind won’t stop,
racing through the worry.
And right when I realize,
I need to let you go,
I wake up,
to my room aglow.
I realize,
it was just a memory of you,
Someone I barely even knew.
I loved someone that you made up,
I'd only see the real you when you drank from your devil’s cup.
Now I lie awake,
remembering the lies,
from a time when I would lie awake and cry.
I used to think our love was real,
and what’s funny now,
is that pain I used to feel,
crept away like the setting sun.
And now I roll over,
and fall fast asleep,
because my pillow is now dry,
I no longer weep.
Isabelle Bauer studies Digital Media Arts at Bridgewater College


Broken Dreams and Waking Truths

Herbst, Samantha

Philomathean 
Volume 3 MMXXIV: Where Our Dreams Take Us Article 34 
2-14-2024 
This Plane of Existence pt. 2 
Samantha Herbst 
sherbst@eagles.bridgewater.edu 
Follow this and additional works at: https://digitalcommons.bridgewater.edu/bc_philomathean 
Recommended Citation 
Herbst, Samantha (2024) "This Plane of Existence pt. 2," Philomathean: Vol. 3, Article 34. 
Available at: https://digitalcommons.bridgewater.edu/bc_philomathean/vol3/iss1/34 
This Fiction is brought to you for free and open access by the Journals and Campus Publications at BC Digital 
Commons. It has been accepted for inclusion in Philomathean by an authorized editor of BC Digital Commons. For 
more information, please contact rlowe@bridgewater.edu. 
This Plane of Existence pt. 2
Sammie Herbst
There I stood outside the house as the wind blew through my hair. The blue dress I wore
was the nicest one I had. It was chilly that day, but I didn’t mind. This was no ordinary day, for
there were visitors. Liesl, as well as Franz, had brought a carriage to take us away for good. We
had everything ready the night before, so Charles and Lorenz were saying goodbye to the few
belongings that they couldn’t take with them. I, on the other hand, waited outside.
Closing my eyes, I waited. He promised he’d come back, and I believed his promise, so
when he stepped forward, I almost thought it was real. My friend’s brother was older, maybe a
year older than Charles. I didn’t remember much of him when we left, but I did remember pieces
of his personality. The way he took care of his parents when they got sick was admirable. Though
I was closer to his younger sister, I always admired him.
“Franz, are you going to kiss me or not?” I asked playfully. It didn’t take long before he
answered without words. This was new for me. I was almost fifteen, and though I had about a
month or two left, I felt much older than I really was. Yet, I didn’t really know if I felt anything for
him or if I was simply wanting a way out of Mutter’s life.
After a moment or two, he took my hand and ran back to the house. Before he could kiss
me again, I heard Mutter’s voice. Suddenly, Franz faded away as Mutter backed me into the wall,
saying I betrayed her. Bringing Franz and his sister to the house meant I didn’t love her and that
I was abandoning her. Though I tried to protest that it wasn’t true, she screamed and cut off my
hair until there was nothing left. Then, an ax appeared in her hand, and she swung in with all her
might, meeting with my flesh.
...
Suddenly, my eyes opened, and I sat up in bed, screaming at the top of my lungs. I had no
idea why I was screaming, but it must have been some horrifying nightmare. No one came to see
if I was alright, so I wondered what was going on.
The sun was out, and it looked to be almost noon. I had no idea why I had slept so long or
why no one came to wake me. Going to the window, I looked out to see Charles doing laundry
by himself. Lorenz played in the grass with imaginary figures. When I called out, Charles
seemed to ignore it, as if angry that I wasn’t helping him. Lorenz, however, looked up at me with
bright eyes. He got up in excitement and started hollering my name. Charles quickly grabbed
him and told him it was just his imagination. Pointing to the window, he said no one was there.
Backing away, I believed it was a dream. It had to be. It couldn’t be true. It simply
wasn’t.
“Charles can’t see you. The fact that Lorenz can is a miracle to me.” An unfamiliar voice
said from behind me.
Spinning around, I noticed a tall man, maybe only thirty or so, but he seemed
recognizable. As I went through my memory, I began to recognize the face. A face that had been
dead since I was very young. This was Papa.
“Papa?”
Nodding his head, he came to my side. We both noticed that Lorenz could see him too,
but Charles refused to listen to any more nonsense that someone was in my window.
“Why can’t he see me? What happened?”
Papa sighed. “You died last night, Asia. I wish I could tell you how, but I really don’t
know. They sent me to make your passage into Heaven easier.”
Laughing at him, I refused to believe it. My only words were that this had to be some
kind of crazy dream. He kept telling me that it wasn’t a dream, that everything I was seeing was
true, but I wouldn’t believe him. How could I be dead if I had no memory of dying? The idea of
it was preposterous. When I tried opening the door, I had no grasp; I couldn’t move through it or
even turn the handle. I couldn’t leave. I wasn’t going to get out. Was I to be an eternal prisoner in
this room? Was there nothing left for me?
Sinking to the ground, I began to cry. After a moment or two, Papa hugged me. He was
aware of my frustrations. Did he have this same experience when he died? Was he not aware of
his death until someone came to tell him? It had been years since that fateful day when a
postman gave us the letter that said Papa was dead. I was only about six at the time and I was
barely capable of understanding what was going on. What was I to do?
After I had worn out my tears, Papa looked at me. He sighed. “Asia, there’s something
your mother didn’t tell you. It’s about the three of you.” He looked down, as if ashamed of
himself. “When I met your mother, I was already a married man in Vienna. It was an arranged
marriage to a woman who I had already split from. We had one son from our wedding, but she
had left and gone to live with her parents, taking my son with her. When I met your mother, I
tried to obtain a divorce from my wife, but she wouldn’t have it.” He paused as he walked over
to the window. “I took your mother to Salzburg. She believed we were married, but I knew the
truth. I treated her as my wife, and we lived together, but she never knew, and I never wanted any
of you to ever know you were illegitimate. Your mother got the house, but I put it in my will that
it would go to my first son. It went to Charles, but then it didn’t.”
Holding myself, I turned away. It was horrifying; nothing was as it seemed. There is
nothing more horrifying than when you have to die in order to learn you’re illegitimate.
My father spent my first few years lying to us, and then Mutter spent my final years lying
to us. Oh, how I wanted to throw something at him, but I couldn’t touch anything anymore,
which only made things more frustrating for me.
Screaming, I rocked myself in comfort. My father held me as though I was a little child
again, though I had ceased being a child when he died. Though I screamed at him to leave me
alone, I couldn’t bear to have him gone. It was such a mix of emotions. After all, I was dead, and
so was he. It seemed only Lorenz was able to see me, but unlike me, he was still alive. He was
alive but not well. Oh, how I wanted that again. My adolescent life was horrible, but I still
wanted to live. I wanted to hold my baby brother in my arms, and I wanted to see Franz, though I
didn’t really know why.
Suddenly, the door opened, and Mutter entered the room, putting a box on my bed. She
didn’t see either of us and started shuffling through her pockets as she started searching for
something. Before she found whatever it was that she was looking for, I turned to the door and
sprinted out. My father yelled for me, but I ignored him. Somehow, I managed to make it down
the stairs and to the backdoor. Neither of my brothers noticed me as I made my way to them.
Lorenz was too lost in his mind, and Charles simply stared at my window, probably watching
Mutter.
We were hidden there because we shouldn’t have existed. My brothers didn’t know we
were illegitimate. They didn’t know, and now they were going to die too. Now that I was gone,
Lorenz’s candle would cease, followed by Charles. There was no existence left for me, but I had
to make sure they didn’t meet the same fate I did. There was the small matter of learning what
my fate actually was.
I remember reading Liesl’s letter, saying she and Franz would be here in a week, and then
there was nothing but black after. She was going to get them out, even if I couldn’t, but I
couldn’t help but cry. If they met the same fate as me before Liesl or Franz got there, my afterlife
would be wasted. Then I knew.
Mutter had a box when she unlocked my room. Whatever was in that box could help
them get out. It would unravel my fate. Yet, Lorenz was the only one who could see me. He was
my key to unlocking what happened.
“Boys, I made you something. Please come in the house.”
Lorenz immediately ran in, though he couldn’t help but glance at me briefly. Charles,
however, begrudgingly finished his chores before making his way to the house. He didn’t even
notice me watching him. Oh, how I wanted to scream for his attention! Death was nothing but a
pain. I had almost no control, and I was basically gone. There was no coming back from life, and
no one would ever hear or see me again. My body was gone. I was no longer on the same plane
as my brothers. It was as if that never really existed.
Following them into the house, I watched from the doorframe as Mutter served them
fresh meat. She looked slightly pale as she served it but said nothing. When the food was ready,
she had my brothers say their prayers before leaving for the day. My brothers happily devoured
the meat before going back to everyday life. Charles began his chores again, and Lorenz began
searching for me. At that, my heart began to ache for him.
...
Two miserable days went by. My father kept trying to encourage me to continue on with
him to Heaven, but I wasn’t finished yet. Lorenz had gotten sick again, and Charles wasn’t much
healthier.
Lorenz called out for me many times, and I tried to comfort him the best I could, though
there was little I could do anymore. While Charles was out in the garden trying to find something
new to feed Lorenz, I stayed by his side and sang to him. I did my best to hold in my tears,
fearing he would learn that I really was dead.
Though I stayed at his bedside, I stopped singing the moment Charles entered the room.
He looked as though he was about to die. I couldn’t bear to see either of them die when my soul
couldn’t move on. I could feel their pain, and I could see their hopes and dreams were crushed.
Papa stood next to me. “Come along, my child. There is nothing else to see here.”
When he tried to lead me away, I smacked his hand away and approached my breathing
brothers eagerly. Lorenz began to cry, unsure of himself. He kept asking Charles for me, but he
looked at me as he said it. I knew he wanted me to hold him, but it was too late for me. Yet, I had
to ensure it wasn’t too late for him.
“Asia left us, Lorenz. Mutter said so, alright? It’s been four days now. We’ve got to get
by without her.” At that, I felt puzzled. Hadn’t it been only three nights since my mysterious
death?
Looking over at me, Lorenz began to protest. “But Charles. She’s right there. I see her!
She and some man are watching us, and they’re both crying. Charles, please just look at the
window.”
My brother did look, but only for a brief second. Turning back to Lorenz, he shook his
head. “There’s no one there.”
Lorenz cried as he pointed at me. My job as mother should have been done, but Lorenz
still needed me. No matter what, he needed me more than anything else.
For some reason, I smiled softly. Approaching him, I shushed him to the best of my
ability and sang for a moment or two before speaking. “Lorenz, I need you to tell Charles to open
my door for me, please. There’s something in there that I need, but I can’t get it anymore.”
“Asia!” Papa hissed. “We do not allow the living to do our bidding.”
Both Lorenz and I ignored him. Lorenz looked at me before speaking to Charles: “We
need to see Asia’s room. She needs something in there! Please, Charles!”
“I’m not going in there!” My brother nearly screamed. “She abandoned us, Lorenz. She’s
never coming back!”
...
In the middle of the night, Lorenz got up and left his room. Sitting with my arms around
my legs, I looked up as I saw him leave. Trying my door, he pulled and pulled with the little
strength he had. Yet he couldn’t. Papa told him to stop, but before he could say more, Charles left
his room to find Lorenz. For a moment or two, Charles held Lorenz back, telling him that he
needed to stop. Then, for a brief moment, his eyes widened as he looked in my direction, almost
as though he saw me. At that, he let Lorenz go.
Charles then got some wire to pick at the lock. He had Lorenz ensure that Mutter wasn’t
behind us as he worked his way through the lock. It finally opened, revealing the most horrifying
thing I would ever find. Charles closed the door behind us at that moment to ensure Lorenz
wouldn’t see my skeleton. The skeleton on the bed, laid out as if waiting for sleep, looked as
though it had been dead for months. It smelled like death and was cleaned of everything.
Though I was horrified to see my decaying skeleton, it took me a moment or two to
realize what I was really looking at. Their lunch. Mutter did what she had to do to get rid of any
evidence that the skeleton was mine.
I turned away in horror. My father again held me as I cried. Mutter wanted to kill us, just
as I feared. Now, she was hiding the evidence through us.
Lorenz screamed outside the door. I couldn’t see what was going on, but I could only
assume it was Mutter. Slamming open the door, she looked at Charles with such hatred. All I
wanted to do was scream at her. How could she? Papa watched her with horror and sadness. It
seemed like even he couldn’t quite comprehend it.
At that moment, Lorenz screamed, understanding that the bed held my skeleton and I was
really dead. Yet, my thoughts were on her. She was going to kill them, just like she killed me. It
came back to me. She hadn’t killed me the night she found the letter, but she didn’t know that.
My body was broken, and I spilled blood after my head slammed into the bedpost. At first
glance, she would’ve assumed I was dead.
Without a thought, she dragged my half-dead body down the stairs. My body hit the stairs
just loud enough to wake Lorenz, who started screaming bloody murder. As I began to wake up,
she hit my head again, this time with the intent to kill. Yet, I was alive, but unconscious.
Later, I began to dream of Franz and how different we each were and his kiss, something
I would never have again. Yet as I dreamt the whole dream again, I woke to Mutter chopping off
my hair and cutting me with the ax, just as I dreamed. The ending wasn’t a dream. It was
happening in real-time. Anguish filled me until the second I died. Where it was remains
unknown to me. But the existence of my last memory on that plane of existence was the last
thing I would ever know.
...
Death is a funny thing. It’s such a strange feeling, almost as though you’re alive but
eternally cold and eternally divided. It’s never a welcoming feeling, and one I would advise you
never to experience if possible. Yet, I know it’s unavoidable. After all, God made human beings
as mortals of this plane of existence.
Rage filled my body as Mutter started beating Charles. Letting go of my father, I felt a
presence stronger than anything I felt since my death. Screaming, I saw both Mutter and Charles
look at me with such horror and shock written across their faces as all the energy I had left filled
me. My soul was now in their plane, approaching Mutter with such speed. Without a thought, I
tackled her to the wall, and with one push, I threw her body through the closed window. And just
like that, Mutter crumbled into the ground with a loud crunch. Just as Mutter killed me, I killed
her.
Even as Papa finally takes me with him to Heaven, I look back at my time on Earth. It
was such a dismal existence, but one I would never change.
...
I watched her grave as the rain fell. Franz and I buried Asia an hour ago. Mutter was left
in the house after we burned it. After everything she did, we never wanted to remember her
again. Lorenz said that he had heard everything Asia had reported about the sins Mutter had
committed. I didn’t quite believe him, but after Asia’s ghost shoved Mutter out the window, I can’t
doubt it anymore. There was nothing we could do after burying her. Liesl held Lorenz as Franz
drove the carriage away. We were to never see the house again; Asia’s grave was the only thing
in sight.
Samantha Katlyn Herbst studies Professional Writing and Music at Bridgewater College


This Plane of Existence pt. 2

This research investigates the synthesis of α-chloro-β-lactone molecules, focusing on the production, isolation, and purification of two precursor compounds from chloroacetic acid and substituted benzaldehydes. While multiple methods were explored, including EDC, DIC, and DCC catalysis, DCC proved to be most effective in producing higher yields. However, challenges in purification arose due to the formation of byproducts, particularly with DCC, prompting further investigation for efficient extraction and purification techniques. DCC, however, shows a promising route for α-chloro-β-lactone synthesis, despite purification complexities

Ellis, Matthew

Bridgewater College 
BC Digital Commons 
ASPIRE 2024 ASPIRE - Arts, Scholarship, Performance, Innovation & Research Excellence 
Spring 2-15-2024 
Purification and Isolation of α-Chloro-β-Lactone Precursor 
Molecules 
Matthew Ellis 
mellis@eagles.bridgewater.edu 
Follow this and additional works at: https://digitalcommons.bridgewater.edu/aspire_2024 
 Part of the Medicinal-Pharmaceutical Chemistry Commons, Organic Chemicals Commons, Organic 
Chemistry Commons, and the Pharmaceutical Preparations Commons 
Recommended Citation 
Ellis, Matthew. “Purification and Isolation of α-Chloro-β-Lactone Precursor Molecules.” Senior Honors 
Projects, Bridgewater College, 2024. 
This Honors Project is brought to you for free and open access by the ASPIRE - Arts, Scholarship, Performance, 
Innovation & Research Excellence at BC Digital Commons. It has been accepted for inclusion in ASPIRE 2024 by an 
authorized administrator of BC Digital Commons. For more information, please contact rlowe@bridgewater.edu. 
 
 
 
 
 
 
 
 
 
 
 
Purification and Isolation of  
α-Chloro-β-Lactone Precursor Molecules  
 
2/4/2024 
 
Matthew Ellis 
 
 
 
 
 
 
 
 
Abstract:  
This research investigates the synthesis of α-chloro-β-lactone molecules, focusing on the 
production, isolation, and purification of two precursor compounds from chloroacetic acid and 
substituted benzaldehydes. While multiple methods were explored, including EDC, DIC, and 
DCC catalysis, DCC proved to be most effective in producing higher yields. However, 
challenges in purification arose due to the formation of byproducts, particularly with DCC, 
prompting further investigation for efficient extraction and purification techniques. DCC, 
however, shows a promising route for α-chloro-β-lactone synthesis, despite purification 
complexities. 
Introduction:  
β- lactones are a class of molecules readily found in nature. Their notoriety in the 
chemistry community comes from its frequent structure found in naturally occurring antibiotics. 
Oxazolomycin and Neooxazolomycin are antibiotics produced by Streptomyces species which 
have been used to treat P-388 leukemia and gram-positive bacteria1. The lactone molecule in 
some cases serves as the backbone for multiple antibiotic molecules.  
 Although four membered lactone rings are abundant in nature the synthesis of these 
molecules in labs have proven difficult. Four members rings are highly strained molecules with 
bond angles of around 60° and 90°. Researchers have devised highly selective substrate catalyst 
methods to form these complex molecules. The use of a catalyst called [(N,N‘-bis(3,5-di-tert-
butylsalicylidene) phenylenediamino)Al(THF)2][Co(CO)4] ([(salph)Al(THF)2][Co(CO)4]) was 
used to produce a β- lactone ring from an epoxide compound2. Although these catalysts exist, 
they are highly selective for formation of lactones from epoxides. To produce a more novel β- 
lactone, molecules such as 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), N,N′-
Dicyclohexylcarbodiimide (DCC), and N,N'-Diisopropylcarbodiimide (DIC) could be viable 
options.  
 EDC is readily used as a crosslinking catalyst for carboxylic groups in antibodies and 
subsequent formations of amide bonds 3. DCC and DIC have similar mechanisms to form lactone 
rings however they are more stable alternatives as catalyst due to symmetrical structure of the 
alkane ends. Carbodiimides largely react to many functional groups which makes choosing 
reaction conditions critical for successful synthesis of products4.  
 The most common forms of product isolation are acid or base work ups to force 
compounds into organic or aqueous solvents. For most compounds, these isolation steps work 
with subsequent rotary evaporation. β -lactone molecules, however, prove difficult when using 
substituted benzaldehydes molecules. For compounds as complex as β-lactones in addition to 
highly reactive reagents, column purification may be needed. Flash chromatography allows for 
fast separation of complex molecules as used in the separation of bioactive compounds in citrus 
fruits such as flavonoids, limonoids, carotenoids, amines, etc5.  
 In this project we looked to find a simple method of producing, isolating, and purifying 
α-Chloro-β-Lactone molecules product 3-Chloro-4-phenyl-2-oxetanone and 3-Chloro-4-(4-
flourophenyl)-2-oxetanone precursor molecule from Chloro-3-hydroxy-3-phenylpropanoic and 
2-Chloro-3-(4-flourophenyl)propanoic acid.  
 
 
 
 
 
Experimental: 
150mL of ether were added to a 250mL round bottom flask under nitrogen. 0.9457 g of 
Chloroacetic Acid (10 mmol, 1 equiv) was added with stir bar and cooled to 0°C under nitrogen. 
9.750mL of Bromo-dicyclohexylborane (21.78mmol, 2.2 equiv) were added to reaction flask 
with 3.10mL of triethylamine (21.78 mmol, 2.2 equiv) and cooled to -78°C. 1.1mL of 
benzaldehyde (10.9 mmol, 1.1 equiv) were added to reaction flask and stirred for 30min. 
Reaction was warmed back to 0°C a stirred for 1 hour. Base quenching and acid workup 
produced a slightly pink crystal product 2-Chloro-3-hydroxy-3-phenylpropanoic acid (1.2418 g, 
55%) racemic (52.44%, 47.56%) was confirmed using 1H NMR (60 MHz, ) δ 5.27 (d, J = 6.2 Hz, 
1H), 4.65 (d, J = 5.8 Hz, 1H).  
 10mL of chloroform were added to a 100mL round bottom flask and placed under 
nitrogen. 0.4080g of 2-Chloro-3-hydroxy-3-phenylpropanoic acid (2 mmol, 1 equiv) was added 
with 0.4209g of EDC (2.2 mmol, 1.1 equiv) and allowed to stir. Reaction was monitored with 
TLC and purified with column chromatography to give a clear oily product 3-Chloro-4-phenyl-2-
oxetanone 1H NMR (300 MHz, CDCl3) δ 8.18 – 8.09 (m, 1H), 7.49 (dd, J = 13.8, 6.2 Hz, 1H), 
1.69 – 1.39 (m, 1H), 1.28 (d, J = 3.6 Hz, 15H), 1.03 – 0.82 (m, 7H). Product was not recovered 
from column purification. The procedure was repeated with acid quenching and base work-up 
but produced no product.  
A 150mL of ether were added to a 250mL round bottom flask and placed under nitrogen 
with stir bar. 0.9457 g of Chloroacetic Acid (10 mmol, 1 equiv) was added and cooled to 0°C. 
9.750mL of Bromo-dicyclohexylborane (21.78mmol, 2.2 equiv) were added to reaction flask 
with 3.10mL of triethylamine (21.78 mmol, 2.2 equiv) and cooled to -78°C. 1.18mL of              
4-flourobenzaldehyde was added to reaction flask and stirred for 30min. Base quenching and 
acid workup produced a yellowish oil product 2-Chloro-3-(4-flourophenyl)propanoic acid 
(1.3308g, 55%) racemic(52.89%, 47.11%) was confirmed using 1H NMR (300 MHz, CDCl3) δ 
7.43 – 7.31 (m, 4H), 7.06 (td, J = 8.7, 2.2 Hz, 4H), 5.65 (s, 6H), 5.26 (d, J = 5.0 Hz, 1H), 5.02 (d, 
J = 8.2 Hz, 1H), 4.50 (d, J = 4.9 Hz, 1H), 4.34 (dd, J = 8.3, 0.6 Hz, 1H), 3.53 (q, J = 7.0 Hz, 6H), 
1.21 (dd, J = 7.3, 6.8 Hz, 8H). 
 A 100mL round bottom flask was filled with 10ml of chloroform and placed under 
nitrogen with stir bar. 0.33mL of 2-Chloro-3-(4-flourophenyl)propanoic acid (2.0mmol, 1 equiv) 
was added to the reaction flask. 0.434g of DCC (2.2 mmol, 1.1 equiv) was added to the reaction 
with 0.150g of Imidazole (2.2 mmol, 1.1 equiv) and allowed to stir. Reaction was monitored with 
TLC. Base workup produced product 3-Chloro-4-(4-flourophenyl)-2-oxetanone (0.2589g, 59%) 
and confirmed using 1H NMR (300 MHz, CDCl3) δ 3.36 (s, 0H), 3.18 (td, J = 9.7, 4.2 Hz, 1H), 
1.91 (dt, J = 8.5, 4.6 Hz, 2H), 1.82 – 1.65 (m, 2H), 1.58 (qd, J = 10.7, 6.8 Hz, 2H), 1.49 – 1.00 
(m, 8H). The same procedure was repeated using 2.9mL of DIC ( 2.2 mmol, 1.1 equiv) to 
produce a clear crystal product 3-Chloro-4-(4-flourophenyl)-2-oxetanone (0.0744g, 17%) and 
confirmed with 1H NMR (300 MHz, CDCl3) δ 10.34 (s, 2H), 7.41 (s, 1H), 7.28 (s, 1H), 7.21 – 
7.02 (m, 1H), 4.70 (s, 1H), 4.00 (dd, J = 14.5, 7.8 Hz, 3H), 3.84 (h, J = 6.5 Hz, 3H), 3.73 (s, 2H), 
1.53 – 1.44 (m, 3H), 1.48 – 1.34 (m, 24H), 1.35 (s, 5H), 1.33 – 1.12 (m, 33H). 
 A 100mL round bottom flask was filled with 10ml of chloroform and placed under 
nitrogen with stir bar. 1.0 mL of 2-Chloro-3-(4-flourophenyl)propanoic acid (6.06 mmol, 1 
equiv) was added to the reaction flask. 1.32g of DCC (6.67 mmol, 1.1 equiv) was added to the 
reaction with 0.455g of Imidazole (6.67 mmol, 1.1 equiv) and allowed to stir. Reaction was 
monitored with TLC until complete. Rotary evaporation followed by flash column failed to 
produce intended product 3-Chloro-4-(4-flourophenyl)-2-oxetanone.    
Reaction Schemes: 
Cl
O
OH
1. CHx
2
BBr, Et
3
N
         Et
2
O, 0oC
2. Benzaldehyde, -78oC, 
30min
OoC, 1 hr
OHOH
O
Cl
 
OHOH
O
Cl
EDC
CHCl
2
O O
Cl
 
Cl
O
OH
1. CHx
2
BBr, Et
3
N
         Et
2
O, 0oC
2. 4-Flourobenzaldehyde, 
-78oC, 30min
OoC, 1 hr
OHOH
O
Cl
F  
OH
OH
O
Cl
F
DCC or DIC
Imidazole
CHCl
2
O
O
Cl
F
 
OH
OH
O Cl
F
DCC
Imidazole
CHCl
2
O
O
Cl
F
 
 
 
Discussion: 
 The initial testing of 2-chloro-3-hydroxy-3-phenylpropanoic acid with EDC did show 
creation of β -lactone derivative. Column chromatography was utilized to purify the product but 
failed to establish a separation of both diastereomers. When the experiment was run again, EDC 
failed to convert 2-chloro-3-hydroxy-3-phenylpropanoic to intended α-chloro-β-lactone product. 
Base purification did not allow for the extraction of product leading to a net loss.  
Reaction of 2-Chloro-3-(4-flourophenyl)propanoic acid with DCC was the most effective 
in formation of β-lactone. Fluorine’s large size helped stabilize transition phase of acid during   
α-chloro-β-lactone ring formation. Testing of both DCC and DIC showed that DCC produced a 
significantly better yield of 3-Chloro-4-(4-flourophenyl)-2-oxetanone at 59% over DIC’s 17%. 
Purification became a problem as DCC converts to a troublesome byproduct DCU which 
precipitates with the α-chloro-β-lactone product. Acid work up was first used to separate product 
from DCU but failed to show product separation. Another purification technique was used with 
subsequent roto-evaporation for solvent removal and flash chromatography. The solvent system 
used was hexanes cooled to 0°C, however, four to five cycles of chromatography failed to 
produce the expected product. This may be attributed to minimal affinity of α-chloro-β-lactone 
precursors with hexanes solvent.  
Researchers found that there is another practical method of β-lactone synthesis by using 
Lewis acid catalyzed [2 +2] cycloadditions with carbonyl compounds and β-lactones also result 
from addition reactions involving ynolate anions6. Purification may need to be on a larger, more 
complex scale to fulfill this sort of procedure. DCC looks to be the route for the best production 
of α-chloro-β-lactone precursor molecule despite challenges with by-product formation. Further 
research can be done on the extraction of DCU by product from α-chloro-β-lactone precursor, 
however, the high yield rate of DCC poses a complex dilemma of product and by-product.  
 
Conclusion:  
This study highlights the synthesis of α-chloro-β-lactone precursor molecules using DCC 
as a catalyst, revealing both the successes and challenges encountered in the process. Although 
DCC produced the desired α-chloro-β-lactone product 3-Chloro-4-(4-flourophenyl)-2-oxetanone, 
purification complexities stemming from the formation of DCU byproduct posed significant 
challenges. Despite attempts to overcome purification challenges through acid workup and flash 
chromatography, achieving complete isolation of the target compound proved difficult. Further 
research aimed at finding more efficient purification techniques and optimizing column 
conditions will help achieve higher α-chloro-β-lactone precursor yield.   
  
 
 
 
 
 
 
 
 
 
 
 
 
References:  
(1) Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemura, D.; Katayama, C.; Iwadare, S.; Shizuri, Y.; 
Mitomo, R.; Nakano, F.; Matsuzaki, A. Structure of Oxazolomycin, a Novel β-Lactone Antibiotic. 
Tetrahedron Lett 1985, 26 (8), 1073–1076. https://doi.org/10.1016/S0040-4039(00)98515-0. 
(2) Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. Synthesis of β-Lactones:  A 
Highly Active and Selective Catalyst for Epoxide Carbonylation. J Am Chem Soc 2002, 124 (7), 
1174–1175. https://doi.org/10.1021/ja017434u. 
(3) Vashist, S. K. Comparison of 1-Ethyl-3-(3-Dimethylaminopropyl) Carbodiimide Based Strategies to 
Crosslink Antibodies on Amine-Functionalized Platforms for Immunodiagnostic Applications. 
Diagnostics 2012, 2 (3), 23–33. https://doi.org/10.3390/diagnostics2030023. 
(4) Azzi, A.; Casey, R. P.; Nałȩcz, M. J. The Effect of N,N′-Dicyclohexylcarbodiimide on Enzymes of 
Bioenergetic Relevance. Biochimica et Biophysica Acta (BBA) - Reviews on Bioenergetics 1984, 768 
(3–4), 209–226. https://doi.org/10.1016/0304-4173(84)90017-X. 
(5) Uckoo, R. M.; Jayaprakasha, G. K.; Patil, B. S. Rapid Separation Method of Polymethoxyflavones 
from Citrus Using Flash Chromatography. Sep Purif Technol 2011, 81 (2), 151–158. 
https://doi.org/10.1016/j.seppur.2011.07.018. 
(6) Danheiser, R.; Nowick, J. A Practical and Efficient Method for the Synthesis of β-Lactones. J. Org. 
Chem 1991, 56, 1176–1185. 
  
 
 
 
 
 
 
 
 
 
 
 
 
 
ADDENDA - Purification and Isolation of α-Chloro-β-Lactone Precursor Molecules 
ME001 - 2-Chloro-3-hydroxy-3-phenylpropanoic acid 
1H NMR            
OHOH
O
Cl
 
 
1H NMR (60 MHz, ) δ 5.27 (d, J = 6.2 Hz, 1H), 4.65 (d, J = 5.8 Hz, 1H). 
 
 
 
 
 
 
OHOH
O
Cl
 
 
52.44% and 47.56% Racemic  
 
 
 
 
 
 
 
 
13C NMR 
OHOH
O
Cl
 
 
13C NMR (15 MHz, ) δ 128.26, 128.11, 126.99, 74.15, 63.64. 
 
 
 
 
 
 
ME002 - 3-Chloro-4-phenyl-2-oxetanone 
1H NMR            
O
O
Cl
 
 
1H NMR (300 MHz, CDCl3) δ 8.18 – 8.09 (m, 1H), 7.49 (dd, J = 13.8, 6.2 Hz, 1H), 1.69 – 1.39 
(m, 1H), 1.28 (d, J = 3.6 Hz, 15H), 1.03 – 0.82 (m, 7H). 
 
 
 
 
 
 
13C NMR 
O
O
Cl
 
 
13C NMR (75 MHz, CDCl3) δ 133.72, 130.19, 128.48, 34.67, 31.94, 31.60, 29.71, 29.37, 25.28, 
22.70, 22.66, 20.69, 14.11, 11.43. 
 
 
 
 
 
 
 
ME003 – No production of 3-Chloro-4-phenyl-2-oxetanone 
1H NMR 
 
1H NMR (300 MHz, CDCl3) δ 7.46 (s, 2H), 7.40 (s, 3H), 7.28 (s, 2H), 2.85 (s, 1H), 1.27 (s, 5H), 
0.88 (s, 3H). 
 
 
 
 
 
 
 
 
 
 
13C NMR 
 
No Integration of Carbons Detected  
 
 
 
 
 
 
 
 
 
 
 
 
ME004 - 2-Chloro-3-(4-flourophenyl)propanoic acid 
1H NMR           
OHOH
O
Cl
F  
 
1H NMR (300 MHz, CDCl3) δ 7.43 – 7.31 (m, 4H), 7.06 (td, J = 8.7, 2.2 Hz, 4H), 5.65 (s, 6H), 
5.26 (d, J = 5.0 Hz, 1H), 5.02 (d, J = 8.2 Hz, 1H), 4.50 (d, J = 4.9 Hz, 1H), 4.34 (dd, J = 8.3, 0.6 
Hz, 1H), 3.53 (q, J = 7.0 Hz, 6H), 1.21 (dd, J = 7.3, 6.8 Hz, 8H). 
 
 
 
OHOH
O
Cl
F  
 
52.89% and 47.11%   
 
 
 
 
 
 
 
13C NMR 
OHOH
O
Cl
F  
 
13C NMR (75 MHz, CDCl3) δ 170.67, 164.39, 161.24, 161.12, 134.33, 134.12, 134.08, 128.90, 
128.79, 128.39, 128.28, 115.64, 115.63, 115.36, 115.35, 74.66, 73.47, 65.93, 62.94, 59.09, 59.07, 
14.93. 
 
 
 
 
 
ME005 DIC - 3-Chloro-4-(4-flourophenyl)-2-oxetanone 
1H NMR          
 
O
O
Cl
F  
 
1H NMR (300 MHz, CDCl3) δ 10.34 (s, 2H), 7.41 (s, 1H), 7.28 (s, 1H), 7.21 – 7.02 (m, 1H), 
4.70 (s, 1H), 4.00 (dd, J = 14.5, 7.8 Hz, 3H), 3.84 (h, J = 6.5 Hz, 3H), 3.73 (s, 2H), 1.53 – 1.44 
(m, 3H), 1.48 – 1.34 (m, 24H), 1.35 (s, 5H), 1.33 – 1.12 (m, 33H). 
 
 
 
 
 
 
13C NMR         
O
O
Cl
F  
 
13C NMR (75 MHz, CDCl3) δ 42.39, 23.40, 20.56. 
 
 
 
 
 
 
 
 
ME005 DCC - 3-Chloro-4-(4-flourophenyl)-2-oxetanone 
1H NMR                                                      
O
O
Cl
F  
 
1H NMR (300 MHz, CDCl3) δ 3.36 (s, 0H), 3.18 (td, J = 9.7, 4.2 Hz, 1H), 1.91 (dt, J = 8.5, 4.6 
Hz, 2H), 1.82 – 1.65 (m, 2H), 1.58 (qd, J = 10.7, 6.8 Hz, 2H), 1.49 – 1.00 (m, 8H). 
 
 
 
 
 
 
       
O
O
Cl
F  
 
60.71% and 39.29%  
 
 
 
 
 
 
 
 
13C NMR          
O
O
Cl
F  
 
13C NMR (75 MHz, CDCl3) δ 55.73, 34.91, 33.96, 31.54, 30.47, 25.91, 25.66, 25.65, 25.44, 
25.07, 24.96, 24.68, 23.93. 
 
 
 
 
 
 
 
ME006 – No Product for 3-Chloro-4-(4-flourophenyl)-2-oxetanone 
1H NMR 
 
1H NMR (300 MHz, CDCl3) δ 7.28 (s, 3H), 1.28 (s, 2H), 0.90 (s, 1H). 
 
 
 
 
 
 
 
 
 
 
 
13C NMR 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
