Bis(iodozincio)methane as a synthetic tool

Abstract

Bis(iodozincio)methane was prepared from diiodomethane and zinc in the presence of a catalytic amount of lead. The compound showed a high potential as an organic synthetic reagent. The reaction with carbonyl compounds proceeded to give methylenated products. The reagent also reacted with a couple of electrophiles sequentially. The function as Lewis acid is also unique. It coordinated with 1, 2-dicarbonyl compounds in face-to-face manner and assisted the stepwise nucleophilic attack on the carbon center of the reagent; the products are cis-1, 2-cyclopropanediols. A structural study was also examined.

(Communicated by Hitosi NOZAKI, M. J. A., March 12, 2003)