β-Phenylseone α,β-Unsaturated Aldehydes, Efficient Three Carbon Homologating Agents. 1,3-Carbonyl Transposition

Abstract

The easily obtained β-phenylseleno α,β-unsaturated aldehydes react with Grignard reagents and with n-butyllithium leading to the 1,2-addition products, which upon acidic hydrolysis in the presence of silica gel afford the selenium-free α,β-unsaturated carbonyl compounds with 1,3-carbonyl transposition.