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Reactions with lead tetraacetate-I. Oxidation of saturated aliphatic alcohols part 1
No full textWhen oxidized with lead tetraacetate 1-heptanol and 1-octanol undergo cyclization to give as major products the corresponding 2-alkyltetrahydrofurans, accompanied by a small amount of the isomeric tetrahydropyran derivatives. Secondary aliphatic alcohols, under similar conditions, are converted to a mixture of cis and trans 2,5-dialkyltetrahydrofurans
Opening of steroid ring a by means of lead tetraacetate
No full textThe lead tetraacetate oxidation of cholestan-1β-ol and cholestan-1α-ol in benzene solution did not afford cyclic ethers but resulted, in major part, in the opening of ring A with formation of 1,10-seco-aldehydes. In addition, cholestane, cholest-1-ene and cholestan-1-one were also obtained
Reactions with lead tetraacetate. I. Oxidation of saturated aliphatic alcohols. Part 1
No full textIt was recently shown that various steroid alcohols could react with lead tetraacetate in non-polar solvents to give tetrahydrofuran and tetrahydropyran derivatives. cyclization occurring when the position of and the distance between the reacting hydroxyl group and the 8 - or d -methyl, methylene or methine group were favourable to ring closure