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Process for the preparation of organic phosphinesPatent GB944062
AbstractPhosphines are prepared by reacting in an inert organic solvent (a) elemental phosphorus, (b) an organometallic compound RLi or RMgX where X is halogen and R is unsubstituted or substituted C1-12 alkyl, cycloalkyl or unsubstituted or substituted aryl, said substituents being halogen or C1-6 alkoxy and, if desired, (c) an alkyl halide, and, essentially when an alkyl halide is not present and optionally otherwise, hydrolysing the reaction mixture with water or dilute mineral acid when the reaction is completed. Temperatures of 0-150 DEG C. may be used. Primary, secondary and tertiary phosphines may be prepared and if molar ratios of reactants of the order 2(RMgX):1(P4):2(alkylhalide) are used, the product is stated to be a cyclotetraphosphine. The reaction mixture in Example V is treated with LiAlH4 before hydrolysis. Products prepared in examples are: phenylphosphine, diphenylphosphine, triphenylphosphine, butylphosphine, dibutylphosphine, tributylphosphine, naphthylphosphine, dinaphthylphosphine, trinaphthylphosphine, 4-methoxyphenylphosphine, 4-fluorophenulphosphine, octylphosphine, dioctylphosphine, trioctylphosphine, cyclohexylphosphine, dodecylphosphine, butylphenylphosphine, dibutylphenylphosphine, butyldiphenylphosphine, butyl (1-naphthyl) phosphine, butylbis (1-naphthyl) phosphine, dibutyl (3-trifluoromethylphenyl) phosphine, butylbis (3-trifluoromethylphenyl) phosphine, dibutyl (4-methoxyphenyl) phosphine, butylbis (4 - methoxyphenyl) phosphine, dibutyloctylphosphine, butyldioctylphosphosphine, hexyldimethylphosphine, dihexylmethylphosphine, butyl 4-fluoro-phenylphosphine, butylbis (4-fluorophenyl) phosphine, dibutyl 4-fluorophenylphosphine, cyclohexyldihexylphosphine, dicyclohexylhexylphosphine, tridodecylphosphine, dipentylpropylphosphine, dipropylpentylphosphine, trihexylphosphine, dimethyl 6-methoxy - 2 - naphthylphosphine, bis (6-methoxy - 2 - naphthyl) methylphosphine, and butylbis (3-trifluoromethylphenyl) phosphine.ALSO:Naphthalene and 1-butylnaphthalene are among the products when white phosphorus is added to an ethereal solution of 1-naphthyllithium and butylbromide obtained from butyllithium and 1-bromo-naphthalene (Example XXIII).
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