Reactivity of substituted and unsubstituted diphenylphosphonium diylides towards carbonic anhydride derivatives

Article abstract of DOI:10.1016/0040-4020(95)01002-5

The reactivity of diphenylphosphonium diylides was investigated towards carbonic anhydric derivatives. Unsubstituted and substituted non-stabilized diylides react with phenylisocyanate and dicyclohexylcarbodiimide, leading to the formation of new monoylide type intermediates. These last ones react in situ with carbonyl compounds through a Wittig reaction leading respectively to α,β-unsaturated amides and amidines. Substituted semi-stabilized or stabilized diylides, in similar conditions lead to the formation of alkenes. In all the cases a high E stereoselectivity, determined by ¹H-NMR and ¹³-C-NMR, was observed.