- REACTION DES CETONES ACETYLENIQUES AVEC LES PHOSPHITES ET LES AMINOPHOSPHITES EN PRESENCE DE REACTIFS DE PIEGEAGE PROTIQUES. SYNTHESE, MECANISME DE FORMATION ET STEREOCHIMIE D'YLURES DE PHOSPHORANES MONOCYCLIQUES ET DE SPIROPHOSPHORANES.
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Cyclic and acyclic trivalent phosphorus compounds (1, 2, 3, 4) were reacted with activated carbonyl acetylenic compounds as 1-4-diphenyl-2 butyne-1,4-dione; 1-Methoxy-phenyl-4-Phenyl-2-Butyne-1,4-dione; 4-oxo-4-phenyl-Methyl-2-butynoate and 1,3-diphenyl-1-propyne-2-one.All these reaction were performed in presence of protic trapping reagents ZH such as methanol a, phenol b or phtalimid c.All these reactions lead to a very unstable 1,3 dipolar species like which is not detected even at low temperature.This species is protonated instantaneously with the protic trapping reagent ZH giving the following intermediate .Further, Z- may attack the phosphorus atom with formation of a vinylic phosphorane: compounds series A and C, or Z- may attack the electrophilic center of the keto group leading either to ylid formation i.e. compounds serie B or to spirophosphoranes formation i.e. compounds serie D.Mechanisms involved in these reactions are studied.
- El Manouni, D.,Leroux, Y.,Burgada, R.
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p. 2435 - 2450
(2007/10/02)
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