Alkylaryl selenides

Conveniently, the required alkylaryl selenoxide does not have to be isolated. Instead, it is produced in solution by a low-temperature oxidation of the corresponding alkylaryl selenide and eliminated in the same synthetic operation by thawing or gently heating the reaction mixture. 

Certain alkylaryl selenides can be prepared by the electrophilic selenylation of enolates (Figure 4.12 also see Table 13.5). With a subsequent H202 oxidation to produce the selenox-ide followed by the elimination of Ph—Se—OH, one proceeds in a total of two synthetic steps from a carbonyl or carboxyl compound to its a,/J-unsaturated analogue. 

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