Bamford-Stevens Reaction; Shapiro Reaction

W. R. Bamford, T. S. Stevens, J. Chem. Soc. 1952, 4735.

Formation of olefins by base-promoted decomposition of p-toluenesulfonylhydrazones of aldehydes and ketones:

The formation of unrearranged alkenes, generally the less substituted isomers, by treatment of ketone derived p-toluenesulfonylhydrazones with alkyl lithium reagents is known as the Shapiro reaction: R. H. Shapiro, M. J. Heath, J. Am. Chem. Soc. 89, 5734 (1967). Use of N,N-diethylaminosulfonylhydrazones: J. Kang et al., Bull. Korean Chem. 13, 192 (1992).

Silicon directing effect: T. K. Sarkar, B. K. Ghorai, Chem. Commun. 1992, 1184. Reviews: R. H. Shapiro, Org. React. 23, 405-507 (1976); R. M. Adlington, A. G. M. Barrett, Accts. Chem. Res. 16, 55-59 (1983); K. Maruka, H. Yamamoto, Comp. Org. Syn. 6, 776-779 (1991); A. R. Chamberlin, D. J. Sall, ibid. 8, 944-949.