Some reactions of aromatic phosphonous and phosphinous acids

Abstract

The addition of phenyl phosphonous acid PhPH(0)(0H) or PhPfOH)^ is shown to occur at the position of sufficiently activated -unsaturated esters (e.g. acetylene dicarboxyiic ester) and c / - unsaturated ketones but at the carbonyl group of aldehydes. The simplest way of explaining these uncatalysed reactions is to postulate that the acid reacts in the trivalent phosphorus form though it is not detected in the infra-red spectrum. The structures of the compounds obtained have been proved by spectral examinations and by C, H and P analysis. SECTION II Cyclic phosphinous acids (phenoiaphosphine oxides) are obtained from the reactions of PCl^-AlCl with diary1 ethers substituted in the p and p' positions. In investigating the scope of this reaction, it has been shown that: (a) both p and p' positions must be occupied; (b) not all substituents permit the reaction. Suitably substituted phenoxaphosphine oxides should be capable of optical resolution and the preparation of two such derivatives has been attempted.

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