Sulfonate Ester Radical Ion Chemistry
Journal of Organic Chemistry
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.
Hehemann, D. G.; Binkley, R. W.; Masnovi, J. Sulfonate ester radical ion chemistry. J. Org. Chem. 1989, 54, 3256-3258.