Olefin Synthesis by Reductive Elimination Reactions of β-Nitro Sulfides

Abstract

Reductive elimination reactions of β-nitro sulfides with sodium sulfide or tributylstannane provide a new method for the preparation of olefins. α-Nitrostilbenes, which are prepared by the condensation reactions of aldehydes with nitro compounds, are converted into stilbenes on treatment with sodium sulfide in the presence of thiophenol. The reaction proceeds very rapidly at room temperature to complete within 5 min. Allyli calcOhols are readily prepared by the tributylstannane-promoted elimination reaction from γ-phenylthio β-nitro alicohols, which are prepared by the reaction of nitro olefins with thiophenol and aldehydes in the presence of a catalytic amount of a base.