
%0 Journal Article
%A Collins, DJ 
%A Rowley, LE 
%A Swan, JM 
%T Organophosphorus compounds. XIII. Synthesis of some 4-Phenylperhydro-1,4-azaphosphorines
%J Australian Journal of Chemistry
%D 1974/04/01
%V 27
%N 4
%P 841-851
%K 
%R https://doi.org/10.1071/CH9740841
%U https://www.publish.csiro.au/paper/CH9740841 
%X The reaction of phenylphosphonic dichloride with two mole equivalents of vinylmagnesium bromide in tetrahydrofuran at ? 70º gave 72% of divinylphenylphosphine oxide, which when heated under reflux for 6h with a 20% excess of aqueous methylamine or of aqueous allylamine afforded almost quantitative yields of 1-methyl- or 1-allyl-4-phenylperhydro-1,4-azaphosphorine 4-oxide, respectively. These compounds were converted into the corresponding phosphine sulphides in high yields. An attempt to prepare 4-phenylperhydro-1,4-azaphosphorine 4-oxide by the reaction of divinylphenylphosphine oxide with ammonium hydroxide and sodium hydroxide at 100º for 26h gave, instead, a low yield of 4-phenylperhydro-1,4-oxaphosphorinane 4-oxide. Reaction of vinylmagnesium bromide with diphenylphosphinic, diphenylphosphinothioic and phosphoryl chlorides are described. 
