Tetrahedron

Synthesis of thioimidates by insertion of TerT-butylisocyanide into the CS bond of activated sulfides. Rearrangement of thioimidates by 1, 3 C to N migration of an …

G Morel, E Marchand, KHN Thi, A Foucaud

Index: Morel,G.; Marchand,E. Tetrahedron, 1984 , vol. 40, p. 1075

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Citation Number: 8

Abstract

Tert-butylisocyanide inserts into the carbon-sulfur bond of α-cyano sulfides 2-6 to give thioimidates 10-14. The thioimidates can also be obtained via the chlorine substitution of the tert-butylimino chloro sulfides 27-28, which is a more general method. These thioimidates rearrange to E and Z isomers of N-vinylcarbamates 16-20 via a 1, 3 C to N migration of the alkoxycarbonyl group.