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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Organophosphorus compounds. XIII. Synthesis of some 4-Phenylperhydro-1,4-azaphosphorines

DJ Collins, LE Rowley and JM Swan

Australian Journal of Chemistry 27(4) 841 - 851
Published: 1974

Abstract

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.

https://doi.org/10.1071/CH9740841

© CSIRO 1974

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