Lithium, diphenylphosphine

It should be noted that the reactions described above cannot be performed in the reverse order, i.e., preparation of the chlorophosphine followed by reaction with LiAsPhz. The reaction of lithium diphenylphosphine with cfr-l,2-dichloroethylene, even with a large excess of the latter, yields only cw-l,2-bisdiphenylphosphinoethylene and not the chlorophosphine, and while 2-chloroethyldiphenylphosphine can be prepared, its isolation is more difficult, and yields are lower than for the corresponding arsine. ... 

Lithium diphenylphosphine (LiPR2) has also been used to substitute sulfonates on sugar derivatives such as 183 and 185 to yield, after spontaneous oxidation, 184 and 186 (O Scheme 79) [124],... 

Lithium dimethyl cuprate, 209-215 Lithium diphenylarsenide, 341 Lithium diphenyl cuprate, 234 Lithium diphenylphosphide, 340-341, 645 Lithium diphenylphosphinate, 340 Lithium di-n-propyl cuprate, 245 Lithium ethynyltrialkylborates, 324-325 Lithium fluoride, 17... 

S, 3 S)-l,4-Di-0-tosyl-L threitol (52), like the corresponding dimesylate 39, forms the bisepoxide 40 when treated with pulverized potassium hydroxide. Treating 40 with lithium diphenylphosphine followed by ketalization provides (2/ ,37 )-( —)-2,3-(9-isopropylidene-2,3-dihydroxy-l,4-bis(diphenylphosphino)butane (54) [( —)-DIOP] in a yield of 56% from 40 [26],... 

Diphenylphosphine) lithium, 126 Nickel boride, 197 Tributyltin hydride, 316 Zinc iodide, 280... 

Diphenylphosphine)lithium, 126 Nickel boride, 197 Samarium(II) iodide, 270 to 1,2-disubstituted compounds B-3-Pinanyl-9-borabicyclo-[3.3.1]nonane, 249 Titanium(III) chloride, 302 of phosphorus compounds Lithium aluminum hydride-Cerium(III) chloride, 159 of sulfoxides and sulfones Sodium iodide-Boron trifluoride ether-ate, 282... 

Lithium borohydride, 92 (lR,2S)-N-Methylephedrine-0-pro-pionate, 308 Norephedrine, 200 2-Oxazolidones, chiral, 225 (2R,4R)-Pentanediol, 237 Potassium triethylborohydride, 260 Other hydroxy carbonyl compounds (R)-( + )- and (S)-( - )-2,2 -Bis-(diphenylphosphine)-1,1 -binaphthyl, 36 Ketones... 

An additional example utilizing phosphorus nucleophiles employs lithium diphenylthiophosphides and allyl carboxylates and yields allylic diphenylphosphine sulfides (equation 66).2 1... 

A previous description of the synthesis of (CH3)3SiP(C6H5)2 in Inorganic Syntheses1 involves the initial preparation of sodium diphenylphosphide from diphenylphosphinous chloride. This method of preparation of the diphenylphosphide anion requires rigorous conditions and long reaction times. At least two other easier methods of preparation of the diphenylphosphide anion (lithium counterion) are known. One synthesis uses diphenyl-phosphine and n-butyllithium2 as reactants, whereas the second uses triphenylphosphine and elemental lithium.3,4 The second method is described here. 

Allenes are activated by a diphenylphosphine oxide substituent towards nucleophilic substitution at the j3-carbon atom. Lithium dimethyl-cuprate adds quickly to the 1,2-bond to give, on hydrolysis, the olefin in 16-84% yield, according to the nature of the substituents (76). Optimum conditions were not reported. The intermediate a-copper compound resulting from the addition can be dimerized or reacted with methyl iodide [Eq. (106)]. Similar reactions involving methyllithium are complicated. 

Dichlorobis(cyclopentadienyl)titanium-Lithium borohydride, 146 Dichlorobis(cyclopentadienyl)titanium-Trlalkylaluminum, 146-147 Dichloro (1,1 -bis(diphenylphosphine)fer-Tocene] palladium(II), 147 Dichlorobis triphenylphosphine)nickel(II),... 

Secondary aromatic phosphines can be prepared from tertiary phosphines by cleavage with sodium in liquid ammonia, and the detailed preparation of diphenylphosphine by this method has been reported. Diphenylphosphine has also been prepared by the reaction of chlorodiphenylphosphine with alkali metals or with lithium tetrahydroaluminate. This phosphine has been also obtained from diphenyltrichlorophosphorane or tetraphenyldiphosphine-disulfide with lithium aluminum hydride. A faster and easier method of preparation, which gives equally high yields, consists in the cleavage of tri-phenylphosphine with lithium metal in tetrahydrofuran, followed by hydrolysis of lithium diphenylphosphide with water to generate the phosphine. ... 

LisN, Lithium nitride, 22 48 LuCL, Lutetium chloride, 22 39 LuC1sCs2, Cesium lutetium chloride, 22 6 LuCLCs3, Cesium lutetium chloride, 22 6 LuF,gNs06Pi2CnH72, Lutetium(IIl), hex-akis(diphenylphosphinic amide)-, tris(hexafluorophosphate), 23 180 LuNsOisCgHig, Ytterbium(III), trini-... 

Diphenylpentene-l-yne-4-one, 128 Diphenylphosphide, lithium salt, 345 Diphenylphosphine, 345 Diphenylphosphorochloridate, 345-346 Dipbenylphosphoroisothiocyanatidate,... 

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