Journal of Organic Chemistry p. 2733 - 2736 (1983)
Update date:2022-09-26
Topics:
Liskamp, Rob M. J.
Blom, Henk J.
Nivard, Rutger J. F.
Ottenheijm, Harry C. J.
The flash vacuum thermolysis (FVT) of the 4-benzamido γ-sultines 5a and 5b is shown to lead to a mixture of the N-allyl amide 6 and enamides 7 and 8, the allyl amide being the main product.This reaction involves a novel migration of the benzamido group, which is proposed to proceed as depicted in path c of Scheme IV.This proposed mechanism features heterolytic bond fission, accompanied by neighboring group participation.Support for this proposal has been found by flash vacuum thermolysis (FVT) of 5a-d2 (Scheme IV).
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(1982)
