The Stereochemistry of Free-Radical Addition of Thiolacetic Acid to Cyclohexenes1, 2

FG Bordwell, PS Landis…

Index: Bordwell,F.G. et al. Journal of Organic Chemistry, 1965 , vol. 30, p. 3764 - 3768

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Citation Number: 18

Abstract

Free-radical addition of thiolacetic acid to 4tbutyl-1-methylcyclohexene resulted in about 80% of trans-diaxial adduct (SAC group axial) and 20% of cis adduct (SAC. group equatorial). This is explained by assuming that in each instance the AcS. radica1 initiates a perpendicular attack on the C= C bond, but that attack from the “top” side of the cyclohexene molecule is preferred for steric reasone. The radical intermediates formed from addition of ...