Shapiro reaction

What is Shapiro reaction?

The Shapiro reaction is a chemical process that is closely related to the Bamford-Stevens reaction. It involves the formation of unrearranged alkenes, typically the less substituted isomers, through the treatment of ketone-derived p-toluenesulfonylhydrazones with alkyl lithium reagents.

Shapiro reaction
Shapiro reaction


Tosylhydrazones. V. Reaction of Tosylhydrazones with Alkyllithium Reagents. A New Olefin Synthesis.
Robert H. Shapiro and Marsha J. Heath
Journal of the American Chemical Society 1967 89 (22), 5734-5735
DOI: 10.1021/ja00998a601