A Comparison of the Effects of Steric Crowding at Phosphorus on the Steric Course of Wittig Reactions of Stabilised and Semistabilised Ylides
نویسنده
چکیده
The cis-trans ratio of the alkenes formed in Wittig reactions of semistabilised ylides (derived from benzyltriarylphosphonium salts in ethanolic sodium ethoxide) with benzaldehyde, acetaldehyde or trimethylacetaldehyde increases as steric crowding at phosphorus increases. In contrast, the cis-trans ratio of the unsaturated esters formed in the related reactions of the stabilised ethoxycarbonylmethylene ylides decreases as steric crowding at phosphorus increases. The relevance of these results to recent proposals for the mechanism of the Wittig reaction is considered.
منابع مشابه
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
Alkene cis-trans Ratio, Betaine Mechanism, Cycloaddition Mechanism The cis-trans ratio of the stilbenes formed in Wittig reactions of semistabilised ylides (derived from benzyltri(hetero)arylphosphonium salts in ethanolic ethoxide) with benzaldehyde decreases markedly in the series 2-furyl >2-thienyl >phenyl > 1-methylpyrrol2-yl. The 2-furyl group favours a greater proportion of the ci«-isomer ...
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