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Article
Sulfonate Ester Radical Ion Chemistry
Journal of Organic Chemistry
  • David G. Hehemann, Cleveland State University
  • Roger W. Binkley, Cleveland State University
  • John Masnovi, Cleveland State University
Document Type
Article
Publication Date
7-1-1989
Disciplines
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
Citation Information
Hehemann, D. G.; Binkley, R. W.; Masnovi, J. Sulfonate ester radical ion chemistry. J. Org. Chem. 1989, 54, 3256-3258.