Abstract
The carbon-13 nuclear magnetic resonance spectra and substituent effects of several acyclic disulfides and their oxidized derivatives are reported. Oxidation of a disulfide to a thiosulfinate or a thiosulfonante has a deshielding effect on the ..cap alpha..-carbon atom and a shielding effect on the ..cap alpha..'-carbon atom. The chemical shifts of ..cap alpha..- and ..cap alpha..'-carbon atoms of sulfinyl sulfones can best be correlated with the shifts of the ..cap alpha..- and ..cap alpha..'-carbon atoms in the corresponding thiosulfinates. On the basis of /sup 13/C NMR shielding trends, it appears that conformational preferences of all the oxidized derivatives of disulfides are similar. A modified gauche effect is proposed to account for the difference in chemical shifts of the ..cap alpha..-carbon atoms in the oxidized derivatives of disulfides.
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