The Journal of Organic Chemistry

tert-Butyl Cation Formation in the Hydrolysis of 2-Methyl-2-propanesulfonyl Chloride, the Simplest Tertiary Alkanesulfonyl Chloride

JF King, JYL Lam, V Dave

Index: King, James F.; Lam, Joe Y. L.; Dave, Vinod Journal of Organic Chemistry, 1995 , vol. 60, # 9 p. 2831 - 2834

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Citation Number: 24

Abstract

Evidence is presented that the only significant reaction of 2-methyl-2-propanesulfonyl chloride (1)(a) in water over the pH range 3.5-13.0 or (b) in methanol-chloroform-d is an ionization to the tert-butyl cation (2) and the chlorosulfite anion (ClSOZ-), followed by further reactions of these species. The organic products include isobutylene (31, tert-butyl chloride (4a), tert-butyl alcohol (4b), and, at high pH, 2-methyl-2-propanesulfinate anion (6) and ...

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