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.
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[Kusuyama,Y. Bulletin of the Chemical Society of Japan, 1979 , vol. 52, p. 1944 - 1949]