J. King, J. Y. Lam, G. Ferrazzi
Feb 1, 1993
Citations
0
Influential Citations
3
Citations
Journal
Journal of Organic Chemistry
Abstract
Cyclopropanesulfonyl chloride (1) he been synthesized and its reactions examined to see if the three-membered ring leads to unusual reactions in either 1 or the corresponding sulfene, cyclopropanethione S,S-dioxide (2). pH-rate profiles, primary kinetic isotope effects (KIE's), and pH-product ratio experiments are in full agreement with mechanisms of hydrolysis of 1 like those of a simple alkanesulfonyl chlorides (J. Am. Chem. Soc. 1992, 114, 1743-1749), specifically, (a) below pH 7.2 by S N 2-S reaction with water and (b) above pH 7.3, elimination by hydroxide to form the sulfene (2) which is terapped by (i) water below pH 12.0 and (ii) hydroxide above pH 12.0