Efficient synthesis of isothiocyanates based on the tandem Staudinger/aza-Wittig reactions and mechanistic consideration of the tandem reactions

…, K Hayashi, S Tamai, T Kumagai, Y Nagao

Index: Isoda, Takeshi; Hayashi, Kazuhiko; Tamai, Satoshi; Kumagai, Toshio; Nagao, Yoshimitsu Chemical and Pharmaceutical Bulletin, 2006 , vol. 54, # 11 p. 1616 - 1619

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Citation Number: 13

Abstract

The tandem and stepwise Staudinger/aza-Wittig reactions of several azides were examined in detail. The tandem reaction method (Method I) exhibited superior results in the yield of the corresponding isothiocyanates bearing an electron-withdrawing group than the conventional stepwise method (Method II) which involves the sequential treatment of the azides with triphenylphosphine and then carbondisulfide. The mechanistic consideration ...