Tetrahedron

Environmentally friendly TPDS-mediated free radical ring expansion of α-haloalkyl cyclic β-keto esters

M Sugi, H Togo

Index: Sugi, Masaaki; Togo, Hideo Tetrahedron, 2002 , vol. 58, # 16 p. 3171 - 3175

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Citation Number: 31

Abstract

Reactivities of tetraphenyldisilane (TPDS), tris (trimethylsilyl) silane, and tributyltin hydride in the radical ring expansion of α-haloalkyl cyclic β-keto esters were examined. Among these reagents, TPDS was found most effective for the preparation of medium-sized cyclic compounds in terms of yields and ring-expansion/reduction selectivity.

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