128478-86-4Relevant academic research and scientific papers
Formation and Reactions of Bis(phosphino)succinic Anhydrides
Doorn, Johannes A. van,Frijns, John H. G.,Meijboom, Nico
, p. 479 - 485 (2007/10/02)
A route to 2,3-bis(phosphino)succinic anhydrides and related compounds is described.The compounds are formed by reaction of a secondary phosphine with maleic anhydrides which bear a leaving group at the alkenic carbon atom.The reaction of bromomaleic anhydride with diphenylphosphine proceeds via diphenylphosphinomaleic anhydride.An acid-catalysed Michael addition leads to cis-2,3-bis(diphenylphoshino)succinic anhydride, which in turn rearranges to the trans isomer by an acid-catalysed process.The trans isomer was isolated as a hydrobromide.The formation of diphosphines from the corresponding maleic acids and esters has also been observed.A primary phosphine does not lead to a phosphinosuccinic anhydride.Addition of a base to the bis(phosphino)succinic anhydride generally leads to the elimination of the phosphine moiety.However, the anhydride ring can be opened with sodium methoxide and a diphosphine, with both a carboxylic acid and a carboxylate ester moiety, is formed in moderate yield.Two conformers or isomers of this compound are obtained, both of which decarboxylate readily to give methyl 2,3-bis(diphenylphosphino)propanoate.Co-ordination of the diphosphine system to PtII prevents both the elimination of secondary phosphine and the decarboxylation of carboxylic groups.
