Phosphorus halides organophosphides

The results from reactions with phenyllithium and phenylsodium indicated that the phosphorus-derived organophosphides were of complex structure (6). The alkyl halide reactions demonstrated the presence of structural units having two phenyl groups bonded to phosphorus, yet only small yields of diphenylphosphine were obtained on hydrolysis. Lithium diphenylphosphide was thus ruled out as an important intermediate, since it hydrolyzes cleanly to diphenylphosphine. Moreover, hydrolysis of the organophosphide from plienylsodium and phosphorus failed to give simple phosphine products at all, but reaction of the sodium... 

Biphosphines may be formed by several methods involving the treatment of phosphinous halides with either electropositive metals or organomercury compounds. An additional intriguing approach involves the reaction of metal organophosphides (see Section 3.2) with 1,2-dibromoethane to form the phosphorus-phosphorus bond and extrude ethylene (equation 17). 

The organophosphides derived from phosphorus and organometallic compounds were found to react with alkyl halides in a manner typical of phosphides, to give unsymmetrical tertiary phosphines (6). Thus, phosphorus, plienyllithium, and butyl chloride gave dibutylphenyl-phosphinc and butyldiphenylphosphine in 37% and 44% yields, respectively. 

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