| Abstract
| - Treatment of acrolein diethyl acetal sulfide 8 with methanesulfenyl bromide at low temperatureresults in an efficient thiirane ring opening to a halo disulfide 9. The bromine in this halo disulfideis easily substituted by silver acetate, sodium azide, sodium iodide, and silver nitrate. Treatmentof 9 with tetrabutylammonium acetate yields a novel dehydrohalogenation product 12. Silica gelconverts bromide 9 into a disulfide-substituted version of acrolein 15. The orthogonal-protectedversion of 2-thioglyceraldehyde 13 can be deprotected to a useful form of this aldehyde.
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