Sequential Reduction and Dehydration of Phenacyl-(E)-Styryl Sulfones to Unsymmetrical (E,E)-Bis(styryl) Sulfones

Abstract

β-Keto vinylic sulfones, the key building blocks for the synthesis of the title compounds, were prepared by two different routes. NaBH₄ reduction of these compounds afforded β-hydroxy vinylic sulfones which were dehydrated with acetic anhydride and BF₃·Et₂O to obtain bis(styryl) sulfones. Alternatively, one-pot synthesis of these bis(styryl) sulfones was also achieved directly from β-keto vinylic sulfones by treating with NaBH₄ in EtOH followed by refluxing with concentrated HCl.

Key words

β-keto vinylic sulfones - β-hydroxy-(E)-vinylic sulfones - (E,E)-bis(styryl) sulfones - styrylsulfinate - Knoevenagel condensation

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