Guidelines for the Use of Proton Donors in SmI2 Reactions: Reduction of α-Cyanostilbene

M Amiel-Levy, S Hoz

Index: Amiel-Levy, Mazal; Hoz, Shmaryahu Journal of the American Chemical Society, 2009 , vol. 131, p. 8280 - 8284

Full Text: HTML

Citation Number: 61

Abstract

The reduction of a series of α-cyanostilbenes with SmI2 was studied in THF in the presence of various proton donors. No reaction occurred in the presence of the alcohols TFE, i-PrOH and t-BuOH. In the presence of MeOH, water and ethylene glycol the reactions occurred; however in the presence of water and ethylene glycol they were too fast for kinetic determinations (τ1/2< 1 ms). Reactions with MeOH were first order in SmI2 and first order ...