New Applications of Crown Ethers. I. Primary Alkylamine–Water–Crown Ether System as a Hydroxide Ion Source in the Reduction with Carbonylhydridoferrate Anion

Abstract

Abstract Utility of the primary alkylamine–water–crown ether system as an effective source of hydroxide ion was studied by the reduction of benzylideneacetone with carbonylhydridoferrate anion. Excellent conversion and selectivity for the reduction were attained in a two-phase system (benzene–water) in the presence of dicyclohexano-18-crown-6, comparable to those obtained with use of potassium hydroxide in place of the amine. Effects of several alkylamines and crown ethers were presented. IR examination of pentacarbonyliron–butylamine-water in benzene with or without the crown ether showed that the presence of the crown ether markedly alters the route of formation of the reducing agent (s).