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

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. (C) 2000 Elsevier Science Ltd. All rights reserved.