Chemistry of Cyclopropanols. V. Stereochemistry of Acid-and Base-Catalyzed Ring Opening1, 2

CH DePuy, FW Breitbeil…

Index: DePuy,C.H. et al. Journal of the American Chemical Society, 1966 ,  vol. 88,  # 14  p. 3347 - 3354            

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Citation Number: 82

Abstract

Abstract: cis-2-Phenyl-1-methylcyclopropanol undergoes a bimolecular electrophilic ring opening in acid solution leading to a 60: 40 mixture of 4-phenyl-2-butanone and 3-phenyl-2- butanone. Stereochemical studies on optically active substrate have shown that this SE~ reaction, the breaking of a carbon-carbon bond by a proton, proceeds with retention of configuration. In base the same cyclopropanol rapidly forms only 4-phenyl-2-butanone. ...