Tetrahedron letters

Rearrangement of cyclic alcohols with an adjacent phenylthio (PhS-) group: Migration of a PhS group around a ring

M Hannaby, S Warren

Index: Hannaby, Malcolm; Warren, Stuart Tetrahedron Letters, 1986 ,  vol. 27,  # 6  p. 765 - 768

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Citation Number: 6

Abstract

766 whereas medium and large rings produce only moderate diastereomeric ratios [(8), n= 7, 8, 15,< 2: 1]. Such selectivities have been explained in terms of an electronic interaction between the 0* orbital of the incipient bond and the adjacent high energy CS a bond. 3 In open chain molecules and presumably in very large rings, this is the same as Felkin's model, S with the mediumsized group [the ring for (11») adjacent to the carbonyl group ...