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Reactions des n-phtalimidyl et n-succinimidyl iminophosphoranes avec les composes a triple liaison; acetyleniques actives et α-halonitriles
Authors:Pierre Merot  Claude Gadreau  André Foucaud
Affiliation:Groupe de Recherches de Physicochimie Structurale, équipe associée au CNRS n°389, Université de Rennes, Campus de Beaulieu, 35042 Rennes, France
Abstract:N-Imidyl iminophosphoranes 1 and 2 with electrophilic acetylenic compounds 5 yield phosphoranes that spontaneously gives ring closure with one of the imidyl carbonyl groups. If this imidyl substituent is an unsymmetrically substituted succinimide, the carbonyl group with less steric hindrance undergoes cyclization. Phthalimidyliminophosphoranes react with some α-halonitriles (i) on the positive halogen if the nitrile group is sterically hindered (halonitriles 8a and 8b); (ii) with the nitrile group of 13, which gives an iminophosphorane 14 that has no action on carbonyl groups of imidyl substituent.
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