128256-16-6Relevant academic research and scientific papers
THE REACTION OF DIBENZYLMERCURY WITH SECONDARY PHOSPHINES: PHOSPHORUS-PHOSPHORUS BOND FORMATION VERSUS BENZYL SUBSTITUTION
Yeh, Jesse T.,Avens, Larry R.,Mills, Jerry L.
, p. 319 - 323 (2007/10/02)
In an attempt to find a simple, high yield synthetic method to create a phosphorus-phosphorus bond from phosphorus-hydrogen bonds, we have investigated the reaction of dibenzylmerury DBM with secondary phosphines.The overall reaction is: DBM + R2PH -> toluene + Hg + R2P-PR2.Thus reaction of diphenylphosphine with DBM produces the desired coupled product tetraphenyl diphosphine in 85-90percent yield.In contrast, the reaction of DBM with 1,3-bis(phenylphosphino)propane Ph(H)P-(CH2)3-P(H)Ph produces the benzyl-substituted product rather than the expected cyclic compound 1,2-diphenyl-1,2-diphospholane PhP-(CH2)3-PPh.The dioxide or disulfide of Ph(H)P-(CH2)3P(H)Ph undergoes no reaction with DBM.The bulky 2,4,6-tris(tert-butyl)phenylphosphine ArPH2 with DBM yields diastereomers of the coupled disecondary diphosphine Ar(H)P-P(H)Ar.The reaction of DBM with diphenylchlorophosphine results in a high yield of tetraphenyl diphosphine, but with phenyldichlorophosphine produces the benzyl-substituted product phenylbenzylchlorophosphine.
