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The cis-trans ratio of the stilbenes formed in Wittig reactions of semistabilised ylides (derived from benzyltri(hetero)arylphosphonium salts in ethanolic ethoxide) with benz-aldehyde decreases markedly in the series 2-furyl &gt;2-thienyl &gt;phenyl &gt; 1-methylpyrrol-2-yl. The 2-furyl group favours a greater proportion of the cis-isomer than m-trifiuoro-methylphenyl, whereas the 1-methylpyrrol-2-yl group favours a greater proportion of the trans isomer than p-methoxyphenyl. Similarly, in Wittig reactions of carbonyl-stabilised ylides with benzaldehyde and acetaldehyde, the presence at phosphorus of 2-furyl groups results in a significant increase in the proportion of the cis-alkene compared to that formed from the related triphenylphosphonium ylide.

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The Chemistry of Heteroarylphosphorus Compounds, Part 14 [1] Effects of Heteroaryl Substituents at Phosphorus on the Steric Course of Wittig Reactions of Semistabilised and Stabilised Ylides