%0 Journal Article %J Green Chemistry Letters and Reviews %D 2012 %T Environmentally benign synthesis of beta-hydroxy sulfides using cyclic carbonates catalyzed by large-pore zeolites %A Upare, Pravin P. %A Kinage, Anil K. %A Shingote, Savita K. %A Gupte, Sunil P. %K beta-hydroxy sulfide %K ethylene carbonate %K propylene carbonate %K thiophenol %K zeolite %X

An efficient one-pot synthesis of beta-hydroxy sulfides from thiophenol and cyclic carbonates catalyzed by large-pore zeolites has been reported. Reaction of thiophenol with ethylene carbonate in the presence of the Na-X zeolite catalyst gave the highest yield of 2-(phenylthio)ethanol (100%), while reaction with propylene carbonate a highest yield of regioselective product 1-(phenylthio)propan-2-ol was obtained (97%). Enantiomerically pure 1,2-propylene carbonate gave highly regioselective and stereospecific phenylthiopropanol, demonstrating that original chirality of propylene carbonate is retained. A plausible mechanism has been proposed for zeolite-catalyzed transformation involving a chemoselective nucleophilic attack of thiophenoloxide ion onto the less-substituted carbon of cyclic carbonate. The Na-X zeolite catalyst is recyclable and provides advantages of green chemistry approach to the synthesis of beta-hydroxy sulfides without the use of any solvent.

%B Green Chemistry Letters and Reviews %I TAYLOR & FRANCIS LTD %C 4 PARK SQUARE, MILTON PARK, ABINGDON OX14 4RN, OXON, ENGLAND %V 5 %P 19-26 %8 AUG %G eng %N 1 %3 Foreign %4 1.392 %R 10.1080/17518253.2011.574295