The 3ß,5-cyclo-5ß-cholestan-6-yl radical (6), generated by interaction of triphenylstannane with 6ß-chloro-3ß,5-cyclo-5ß-cholestane (12), undergoes ß-scission by specific fission of the 4,5-bond to give the thermodynamically less stable possible radical product (8). The results of these and earlier experiments indicate that ß-scission of cyclopropylcarbinyl radicals is under stereoelectronic control, and involves a transition state formed by primary interaction of the semi-occupied orbital with a ß?-s* orbital.
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Beckwith et al. (1976) studied this question.