REVERSIBLE AND IRREVERSIBLE ELCB MECHANISMS IN THE HYDROLYSIS OF 2,2,2-TRIFLUOROETHANESULFONYL CHLORIDE - CARBANION INTERMEDIATES IN AQUEOUS ACID

Authors
KING JF GILL MS
Citation
Jf. King et Ms. Gill, REVERSIBLE AND IRREVERSIBLE ELCB MECHANISMS IN THE HYDROLYSIS OF 2,2,2-TRIFLUOROETHANESULFONYL CHLORIDE - CARBANION INTERMEDIATES IN AQUEOUS ACID, Journal of organic chemistry, 63(3), 1998, pp. 808-811
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
3
Year of publication
1998
Pages
808 - 811
Database
ISI
SICI code
0022-3263(1998)63:3<808:RAIEMI>2.0.ZU;2-R
Abstract
Hydrolysis of 2,2,2-trifluoroethanesulfonyl chloride (1) is shown to t ake place by way of the sulfene (CF3CH=SO2), formed by (a) an irrevers ible E1cB process over the pH range 1.8-5 with water acting as the car banion-forming base in the lower pH range and hydroxide anion at highe r pH, and (b) a reversible E1cB reaction in dilute acid.