Neighbouring-group influence on the ring opening of some 2-alkyl-1, 1, 2-tribromocyclopropanes under phase-transfer conditions

LK Sydnes, KFS Alnes, N Erdogan

Index: Sydnes, Leiv K.; Alnes, Karl F. S.; Erdogan, Natalia Monatshefte fur Chemie, 2005 , vol. 136, # 10 p. 1737 - 1749

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Citation Number: 5

Abstract

Summary. Several 2-alkyl-1, 1, 2-tribromocyclopropanes were treated with sodium hydroxide and ethanol under phase-transfer conditions. Ring opening gave mixtures of the corresponding acetylenic diethyl ketals and acetals. When the steric bulk of the alkyl substituent was increased acetal formation dominated, and in the case of 1, 1, 2-tribromo-2- (tert-butyl) cyclopropane, the acetal was formed as the only product.