Radical-chain racemisation of tetrahydrofurfuryl acetate under conditions of polarity-reversal catalysis: possible implications for the radical-induced strand cleavage of DNA

Abstract

Alkanethiols with electron-withdrawing S-alkyl groups and silanethiols act as polarity-reversal catalysts to promote the radical-chain racemisation of (R)-tetrahydrofurfuryl acetate at 60 °C, while simple alkanethiols are ineffective.