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A stereospecific anionic reduction of gem??bromohalocyclopropanes by the dimsyl anion

…, WH De Wolf, F Bickelhaupt

文献索引:Wijsman, G. W.; Wolf, W. H. de; Bickelhaupt, F. Recueil des Travaux Chimiques des Pays-Bas, 1994 , vol. 113, # 1 p. 53 - 60

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被引用次数: 5

摘要

Abstract The reaction of several 2, 2, 3, 3-tetrasubstituted-gem-bromohalocyclopropanes with t-BuOK in DMSO unexpectedly yielded the monohalocyclopropanes in good yield. A closer investigation revealed that this reaction must be initiated by a nucleophilic attack by the dimsyl anion (CH 3 SOCH 3) on bromine with subsequent protonation of the carbenoid intermediate. The reaction occurs rapidly (within 2 minutes) and is not inhibited by radical ...