Environmentally benign synthesis of beta-hydroxy sulfides using cyclic carbonates catalyzed by large-pore zeolites
Title | Environmentally benign synthesis of beta-hydroxy sulfides using cyclic carbonates catalyzed by large-pore zeolites |
Publication Type | Journal Article |
Year of Publication | 2012 |
Authors | Upare, PP, Kinage, AK, Shingote, SK, Gupte, SP |
Journal | Green Chemistry Letters and Reviews |
Volume | 5 |
Issue | 1 |
Pagination | 19-26 |
Date Published | AUG |
ISSN | 1751-8253 |
Keywords | beta-hydroxy sulfide, ethylene carbonate, propylene carbonate, thiophenol, zeolite |
Abstract | 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. |
DOI | 10.1080/17518253.2011.574295 |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 1.392 |