The Journal of Organic Chemistry

Synthesis and cyclization of polymer-supported 12-hydroxydodecanoic thiol esters

S Mohanraj, WT Ford

Index: Mohanraj, Subramaniam; Ford, Warren T. Journal of Organic Chemistry, 1985 , vol. 50, # 10 p. 1616 - 1620

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Citation Number: 29

Abstract

12-Hydroxydodecanoic thiol esters were synthesized on 2% cross-linked polystyrene supports to test the ability of the support to improve yields of intramolecular cyclization to lactone. With mercuric trifluoroacetate in dichloromethane, 0.03 M polymer-supported 12- hydroxydodecanoic thiol ester cyclized to 13% 12-dodecanolide and 19% of the corresponding diolide. Under otherwise similar conditions, 0.01 M model thiol ester gave< ...