Sulfonate Ester Radical Ion Chemistry

Document Type

Article

Publication Date

7-1989

Publication Title

Journal of Organic Chemistry

Abstract

Tosylate ester radical anions in the gas phase cleave the sulfonate S-C bond, resulting in formation of a sulfite anion. This is in marked contrast to the solution- phase chemistry, where cleavage of the sulfonate S-0 bond to produce a sulfonyl radical and alkoxide ion is observed. The difference in reaction pathways is attributable to solvation of the incipient alkoxide anion leaving group.

DOI

10.1021/jo00275a005

Volume

54

Issue

14

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