123. Eschenmoser Coupling Reaction
(Sulfide Contraction)
A. Fischli, A. Eschenmoser, Angew. Chem. Int. Ed. 6, 866 (1967); M. Roth et al., Helv. Chim. Acta 54, 710 (1971).
Formation of vinylogous amides and urethanes by alkylation of secondary or tertiary thioamides with an electophilic agent followed by elimination of sulfur:
References
Synthetic applications: E. Gtschi et al., Angew. Chem. Int. Ed. 12, 910 (1973); O. Sakurai et al., J. Org. Chem. 61, 7889 (1996), T. G. Minehan, Y. Kishi, Tetrahedron Lett. 38, 6811 (1997). Review: K. Shiosaki, Comp. Org. Syn. 2, 865-894 (1991).