A carbon-phosphorus bond cleavage was observed in the reaction of MCl2(PR3)2 (M=Ni, Co, or Pd, R=Ph, n-C8H17) with p-tolyllithium, p-tolylmagnesium halide, lithium aluminum hydride, or magnesium amalgam, and the reactivity was most pronounced with Ni followed by Co and Pd. Reaction of NiCl2(PPh3)2 with p-tolyllithium gave biphenyl and 4-methylbiphenyl, along with 4,4′-dimethylbiphenyl. Phenyllithium was formed in the reaction mixture, and the recovered tertiary phosphine contained tri-p-tolylphosphine, di-p-tolylphenylphosphine, and p-tolyldiphenylphosphine as well as triphenylphosphine. 1-Octene was formed in the reaction of NiCl2{P(n-C8H17)3}2 with p-tolyllithium. Thermal decomposition of Ni(mesityl)X(PEt3)2 (X=mesityl or Br) and Co(mesityl)2(PPhEt2)2 at 30 °C gave vinyl mesitylene.
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