Reductive Dehalogenation of vic-Dihaloalkanes to Alkenes with Sodium Sulfide under Phase-Transfer Conditions

Article abstract of DOI:10.1021/jo00175a031

Reductive dehalogenation of vic-dihaloalkanes to alkenes with aqueous Na2S under phase-transfer catalysis conditions is reported.Debromination reaction occurs at room temperature, giving alkenes in 90percent or >90percent yields.Meso and erythro vic-dihaloalkanes afford only trans olefins and react faster than the corresponding diastereomeric d,l and threo derivatives, which are converted into a mixture of cis and trans olefins. vic-Dichloroalkanes react much more slowly than the bromo compounds, affording the dehydrochlorination products instead of the reductive dehalogenation ones.