The Journal of organic chemistry

Fe (II)-catalyzed imidation of allyl sulfides and subsequent [2, 3]-sigmatropic rearrangement. Preparation of α-branched N-tert-butyloxycarbonyl (Boc)-protected N- …

T Bach, C Körber

Index: Bach, Thorsten; Koerber, Christina Journal of Organic Chemistry, 2000 , vol. 65, # 8 p. 2358 - 2367

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Citation Number: 66

Abstract

Allyl aryl sulfides 1 and 5 were shown to undergo an imidation/[2, 3]-sigmatropic rearrangement reaction upon treatment with N-tert-butyloxycarbonyl azide (BocN3) and catalytic amounts of FeCl2 in CH2Cl2. The N-Boc-protected N-allyl sulfenamides 3 and 21 were obtained in yields between 48 and 75%(12 examples). Whereas the reaction is well suited for the transformation of α-unbranched sulfides to α-branched sulfenamides, the ...