Selenoxide elimination

Selenoxide elimination (also called α-selenation) is a method for the chemical synthesis of alkenes from selenoxides. It is most commonly used to synthesize α,β-unsaturated carbonyl compounds from the corresponding saturated analogues. Selenoxide elimination (also called α-selenation) is a method for the chemical synthesis of alkenes from selenoxides. It is most commonly used to synthesize α,β-unsaturated carbonyl compounds from the corresponding saturated analogues. After the development of sulfoxide elimination as an effective method for generating carbon–carbon double bonds, it was discovered that selenoxides undergo a similar process, albeit much more rapidly. Most selenoxides decompose to the corresponding alkenes at temperatures between −50 and 40 °C. Evidence suggests that the elimination is syn; however, epimerization at both carbon and selenium (both of which are stereogenic) may occur during the reaction. As selenoxides can be readily prepared from nucleophilic carbonyl derivatives (enols and enolates), selenoxide elimination has grown into a general method for the preparation of α,β-unsaturated carbonyl compounds.