Predominant intramolecular Pummerer reactions of substituted benzyl p-tolyl sulfoxides with acetic anhydride.

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概要

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• In the Pummerer reactions of <SUP>18</SUP><I>O</I>-labeled benzyl, and 3,5-dichlorobenzyl <I>p</I>-tolyl sulfoxides with a large excess of unlabeled acetic anhydride in the presence of DCC as acid scavenger, the resulted Pummerer reaction products, the α-acetoxy sulfides, were found to have retained substantial amounts of <SUP>18</SUP><I>O</I>-label of the original sulfoxides, <I>i.e.</I>, nearly a half or more. Meanwhile, when optically active benzyl, 3-chlorobenzyl, and 3,5-dichlorobenzyl <I>p</I>-tolyl sulfoxides were allowed to react with excess acetic anhydride in the presence of DCC, the α-acetoxy sulfides, the Pummerer reaction products obtained, were found to have no optical activity. These observations suggest that the acetoxyl migration from sulfur atom to α-carbon is predominantly intramolecular, however, the α-(<I>p</I>-tolylthio) carbenium acetate ion-pair formed during the reaction prior to racemization is less intimate than those which are formed in the reactions of cyanomethyl and (α-carbonyl-substituted methyl) <I>p</I>-tolyl sulfoxides which give the corresponding highly optically active α-acetoxy sulfides.

• 公益社団法人 日本化学会の論文

著者

• Itoh Osamu

  Department Of Internal Medicine Ii Fukushima Medical College

• Oae Shigeru

  Deparment of Applied Chemistry Faculty of Engineering Osaka City University

• Numata Tatsuo

  Department of Chemistry, The University of Tsukuba

• Yoshimura Toshiaki

  Department of Applied Chemistry, Faculty of Engineering, Osaka City University

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