Tetrahedron Letters

Radical-chain redox rearrangement of cyclic benzylidene acetals to benzoate esters in the presence of thiols

BP Roberts, TM Smits

Index: Roberts, Brian P.; Smits, Teika M. Tetrahedron Letters, 2001 , vol. 42, # 1 p. 137 - 140

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Citation Number: 27

Abstract

Cyclic benzylidene acetals derived from 1,2- and 1,3-diols undergo an efficient ring-opening redox rearrangement to give benzoate esters in the presence of a peroxide initiator and a thiol, which acts as a polarity-reversal catalyst to promote the radical-chain reaction. ... 1,2- and 1,3-Diols are commonly protected as cyclic benzylidene acetals 1 (n=0 or 1) during organic synthesis. 1 In 1962, Huyser and Garcia 2 reported that some simple benzylidene acetals ...