Tetrahedron

Regiospecipicity in the nucleophilic ring opening reactions of gem-dichlorocyclopropylcarbinyl cations

FT DeWeese, DE Minter, JT Nosovitch, MG Rudel

Index: DeWeese, F. Thane; Minter, David E.; Nosovitch, John T.; Rudel, Michael G. Tetrahedron, 1986 , vol. 42, # 1 p. 239 - 244

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Citation Number: 4

Abstract

gem-Dichlorocyclopropylcarbinyl cations, generated under acidic conditions from the corresponding alcohol or alkene, undergo ring opening by nucleophilic attack exclusively at the halogenated carbon when the alternative electrophilic ring carbon is unsubstituted. In one case, a novel trifluoroacetoxydichloromethyl function has been produced and characterized as a masked carboxylic acid chloride.