Reactions of lithium diorganocuprates (I) with oxiranes

CR Johnson, RW Herr, DM Wieland

Index: Johnson,C.R. et al. Journal of Organic Chemistry, 1973 , vol. 38, # 25 p. 4263 - 4268

Full Text: HTML

Citation Number: 106

Abstract

Lithium diorganocuprates have been shown to be highly effective reagents for the nucleophilic ring opening of oxiranes in the trans manner. These reactions occur more rapidly in diethyl ether than in tetrahydrofuran. Evidence and precedent for a mechanism involving the formation of a triorganocopper (II1) intermediate is discussed. The selectivity of lithium diorganocuprates in reactions with substrates containing epoxide along with other ...