Synthesis

A new and efficient epoxide ring opening via poor nucleophiles: indole, p-nitroaniline, borane and O-trimethylsilylhydroxylamine in lithium perchlorate

A Heydari, M Mehrdad, A Maleki, N Ahmadi

Index: Heydari, Akbar; Mehrdad, Morteza; Maleki, Aziz; Ahmadi, Nafiseh Synthesis, 2004 , # 10 p. 1563 - 1565

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Citation Number: 14

Abstract

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-Et 2 O solution. These reactions are fast, convenient, with rather high yields and are carried out at ambient temperatures.