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    High-pressure Diels-Alder reaction. Preparation of [2.2]paracyclophane derivatives

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    High-pressure Diels-Alder cycloaddition reactions of 5-ethenyl[2.2]indeno-paracyclophane with 1,4-benzoquinone, N-phenylmaleimide, and 2-inden-1-one have been studied. Attempts to convert the cycloadducts into the corresponding aromatic helicenophanes failed. All new compounds were characterized by extensive nuclear magnetic resonance (NMR) investigations

    Synthesis of enantiopure angularly condensed [2.2]paracyclophanes containing five-membered rings

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    Optically active angularly condensed [2.2]paracyclophanes containing five-membered rings have been synthesized by a two-step approach based on the Diels-Alder cycloaddition of (S)-(+)-4-vinyl[2.2]paracyclophane. Structural analysis by NMR spectroscopy is presented. These helicenophanes containing a cyclopentane ring show extraordinarily high specific rotations. This phenomenon has been discussed in terms of structural modifications caused by the replacement of the benzene unit with a cyclopentane ring. © 2003 Elsevier Science Ltd. All rights reserved
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