10.2.3 Sulfoxide Elimination

The compound containing an activated C-H bond can underogo reaction with diphenyl or dimethyl disulfide in the presence of base to give substituted sulfide that could be readily oxidized to sulfoxide (Scheme 7). The latter readily undergoes elimination on heating to give α, β - unsaturated carbonyl compound.

Scheme 7

10.2.4 Corey-Winter Olefination

This method gives an effective route for the transformation of 1,2-diol to alkenes. The cyclic thiocarbonate formed from 1,2-diol and thiocarbonyldiimidaole undergoes reaction with phosphorus reagent via a syn elimination to afford alkene (Scheme 8).

Mechanism

Scheme 8

Examples