
%0 Journal Article
%A Brophy, JJ 
%A Gallagher, MJ 
%T Phosphonium salts. II. The reaction of bis-phosphonium salts with metal hydrides
%J Australian Journal of Chemistry
%D 1969/07/01
%V 22
%N 7
%P 1399-1404
%K 
%R https://doi.org/10.1071/CH9691399
%U https://www.publish.csiro.au/paper/CH9691399 
%X Ethane-1,2-bis-phosphonium salts are cleaved by sodium hydride to phos- phines in 55-80% yields with loss of the two-carbon bridge. The reaction is independent of the substituents at the phosphorus atoms. The same reaction is observed with an ethene-1,2-bis-salt and with but- 2-ene-1,4-bis(triphenylphosphonium) dibromide. It is suggested that a phosphorane is formed which subsequently fragments in a manner analogous to alkaline hydrolysis.     Lithium aluminium .hydride behaves similarly but loss of the bridge is competitive with loss of benzyl groups, and yields are generally better (> 70%). 
