A New and Efficient Epoxide Ring Opening via Poor Nucleophiles: Indole, <i>p</i>-Nitroaniline, Borane and <i>O</i>-Trimethylsilylhydroxylamine in Lithium Perchlorate

Abstract

Highly regioselective ring opening of 2,3-dimethyloxirane, 2-epoxyphenylether and allyl(2-epoxymethyl) ether are observed through reactions with poor nucleophiles such as indole, borane, O-trimethylsilylhydroxylamine, p-nitroaniline and sterically hindered tert-butylamine in the presence of 5.0 M lithium perchlorate-Et2O solution. These reactions are fast, convenient, with rather high yields and are carried out at ambient temperatures.