Formation under high-dilution conditions of transient phosphaalkenes by Lewis-base-induced rearrangement of vinylphosphines, a useful entry to cyclic phosphines
Transient phosphaalkenes are formed under high-dilution conditions by Lewis-base induced rearrangement of vinylphosphines. They lead to cyclic phosphines in high yields in the presence of dienes.
A general method for preparing secondary P-alkenyl and P-alkynyl phosphine oxides, compounds unknown so far, involves the condensation of the vinyl Grignard reagent or lithium acetylide on P-chloroaminophosphines followed by acidic hydrolysis of the corresponding vinyl- or ethynylaminophosphines on a solid acid (Amberlyst 15). The few reported chemical properties are mainly related to the strong PH bond activation. Of special interest is the addition of a secondary vinylphosphine oxyde derivative on methyl acrylate which occurs at room temperature without any catalyst.
Gaumont Annie-Claude, Guillemin Jean-Claude, Denis Jean-Marc, J. Chem. Soc. Chem. Commun, (1994) N 8, S 945-946