Phenyldichlorophosphine

Several C1 nuclear quadrupole resonance (n.q.r.) studies have been carried out on chlorophosphorus compounds. - The frequencies observed for phenyldichlorophosphine are similar to those of phosphorus... 

Pentyn-1-ol, 33, 68 Peracetic acid, 33, 79 -Phenetidine hydrochloride, 31, 11 a-Phenoxyacetoacetic acid, 33, 44 Phenylacetamide, 32, 92 Phenylacetic acid, 32, 93, 94 33, 70 imino ether hydrochloride, 32, 94 N-Phenylacetimidochloride, 31, 51 Phenylacetonitrile, 30, 44 32, 92 Phenylacetylene, 30, 72 7-Phenylallylsuccinic acid, 31, 85 7-Phenylallylsuccinic anhydride, 31, 86 Phenylazide, 31,16 Phenylazoacetoacetic acid, 32, 85 Phenyl benzoate, 32, 103 IttZtti-l-PHENYL-l,3-BUTADIENE, 30, 75 7-Phenylbutyric acid, 33, 91 a-PHENYL-a-CARBETHOXYGLUTARO-NITRILE, 30, 80, 82 tt-Phenylcinnamonitrile, 32, 63 Phenyldichlorophosphine, 31, 88 0-PhENYLENE CARBONATE, 33, 74 o-Phenylenediamine, 30, 56, 86... 

The reaction of A-Boc protected amino acids alanine (184) and valine (185) with phenyldichlorophosphine in the presence of NEt3 was reported to lead to the clean formation of essentially one compound in each case, the P-chiral, tricoordi-nated, 1,3,2-oxazaphospholidinones 186 and 187 respectively (Scheme 52) [83],... 

If a higher ratio of alkylating agent to PX3 is used, the dialkyl and trialkyl compounds can also be obtained. At high temperature, the reaction of benzene and PC13 produces phenyldichlorophosphine, CsH5PC12, an intermediate in the preparation of parathion. 

Freshly distilled propanal (4.4 g, 0.075 mol) was added at room temperature over a period of 20 min to a stirred mixture of benzyl carbamate (7.55 g, 0.05 mol), phenyldichlorophosphine (8.95 g, 0.05 mol), and glacial acetic acid (10 ml). The mixture was refluxed for 40 min, treated with 4 N hydrochloric acid (50 ml), and then refluxed again for 30 min. After cooling, the organic layer was removed, and the aqueous layer was boiled with charcoal (2 g) and evaporated to dryness in vacuum. The residue was dissolved in methanol (40 ml) and treated with propylene oxide until a pH of 6 to 7 was attained. The resultant precipitate was filtered, washed with acetone, and crystallized from methanol/water to give pure (l-aminopropyl)phenylphos-phinic acid (4.08 g, 41%) of mp 256-258°C. 

Photolysis of the phosphine (166) gives the benzophosphole (167) in good yield.154 The dilithium aldimine (168) reacts with phenyldichlorophosphine to form the benzophosphazole (169).155... 

Example 54 hydrogen 0-/-(-)-methylphenylphosphinothioate Rp, Sp has been prepared by Michalski et al. from phenyldichlorophosphine [88] by the following sequence of reactions. Phenyldichlorophosphine when allowed to... 

It must be concluded, therefore, that fluorophosphines are strongly reducing, a fact which was confirmed in further attempts at their preparation, using different reagents in the fluorination of chlorophosphines. There was either no reaction at all under the experimental conditions—e.g., with alkali fluorides in benzene as a solvent—or the trivalent phosphorus in the starting chlorophosphine was readily converted to the quinquevalent state—e.g., when phenyldichlorophosphine reacted with sodium fluoride in the presence of an antimony trioxide catalyst in a polar solvent such as acetonitrile to give phenylphosphonic difluoride. Recent Russian work showed that phenyldichlorophosphine was converted into phenyltetrafluoro-phosphorane, C6H5PF4, when it reacted with antimony trifluoride (34),... 

At the time of our investigation the only known coordination compounds of chlorophosphines (aside from phosphorus trichloride complexes) were the nickel-(0) compounds, tetrakis(methyldichlorophosphine)nickel-(0) (20) and tetrakis-phenyldichlorophosphine) nickel- (0) (17). Tetrakis (methyldichlorophosphine) -nickel-(0) is noteworthy in that it represents a still rare example of the direct reaction of a ligand with an elemental transition metal to give a complex, while tetrakis (phenyldichlorophosphine) nickel- (0), like tetrakis (trichlorophosphine) -nickel-(0), was obtained readily via the carbonyl. AD chlorophosphine-nickel-(O) complexes, including the phosphorus trichloride complex, Ni(PCl3)4, are compounds relatively stable in the atmosphere, but show poor stability in almost any organic solvent, even under strictly anaerobic conditions. 

Tetrakis (phenyldichlorophosphine) nickel-(0) does not exhibit any significant absorption in die 1000- to 750-cm.—1 region. 

Platinum(II)15 and palladium(II)16 complexes of phosphorus trichloride undergo solvolysis in water and alcohols to form complexes with orthophosphorous acid or orthophosphite ligands (equation 6). Similar reactions occur between the palladium(II) phenyldichlorophosphine complex (8) and the diols ethyleneglycol and catechol, but new chelate rings are not formed (Scheme 2). Solvolysis also occurs with attack of diphenylphosphinic acid or a similar diphenylchlorophosphine complex (9) (equation 7). The palladium complexes (8) and (9) are unstable to excess methanol, water or base and undergo reduction. Similarly, the phosphorus trichloride gold(I) complex (10) is reduced by water, but forms stable products on reaction with alcohols (equation 8).15 During the above reactions, the phosphorus—metal bond remains intact and the overall process is one of substitution at phosphorus. 

This method was not suitable to prepare phenyIbis (p-dimethylaminophenyl) phosphine (abbreviated as L2). This ligand was prepared in 23% yield by the method of Venanzi and co-workers (10) using the reaction of the lithium derivative from p-bromo-N,N-dimethylaniline with phenyldichlorophosphine. 

Phenyldichloroarsine, AG13 Phenyldichlorophosphine, AG31 Phenyl dimethylaminomethyl ketone, AR97... 

The formation of compounds 18-20 is explained by a two-stage process, where the intermediate product of the reaction (in the case of the reaction with phenyldichlorophosphine) is 3-indolylphenylchlorophosphine, which does not manage to accumulate in significant amounts in the reaction process and is not therefore detected in the 31P NMR spectrum. 

Phenylselenophosphonic dichloride, C6H5PC12. The reagent is prepared by reaction of phenyldichlorophosphine with selenium at 170-175°.1... 

Phenyldichlorophosphine has been prepared by the vapor-phase reaction of benzene and phosphorus trichloride over pumice in a hot tube 2 and by the action of diphenylmercury on phosphorus trichloride.3 The method described here is a Michaelis modification of a Friedel-Crafts reaction.4... 

SYNS PHENYLDICHLOROPHOSPHINE O PHENYL-PHOSPHINE DICHLORIDE PHENYLPHOSPHONOUS ACID DICHLORIDE PHENYLPHOSPHONOUS DICHLORIDE PHENYL PHOSPHORUS DICHLORIDE PHENYL PHOSPHORUS DICHLORIDE (DOT)... 

PHENYL CYCLOHEXYL KETONE see PES750 trans-2-PHENYLCYCLOPROPYLAMINE see PET750 PHENYLDIBROMOARSINE see DDR200 PHENYL DICHLORARSINE see DGB600 PHENYLDICHLOROARSINE see DGB600 PHENYLDICHLOROPHOSPHINE see DGE400... 

Phenyltetrafluorophosphorane was first obtained by the reaction of phenyldichlorophosphine with antimony(V) fluoride or a mixture of antimony(V) chloride and antimony-(III) fluoride. In another method of preparation, phenyl-tetrachlorophosphorane was fluorinated with antimony(III) fluoride. Sulfur(IV) fluoride was used to fluorinate both phenylphosphonic acid and phenylphosphonic difluoride under autogenous pressure. Finally, it was found that phenyltetrafluorophosphorane is formed upon reaction of phenyldichlorophosphine with antimony(III) fluoride, by a simultaneous redox and fluorination reaction. " The last reaction is described below. It is very general in scope and has been employed in the synthesis of a wide variety of tetrafluorophosphoranes. " It may be noted that arsenic-(III) fluoride can be employed similarly as the fluorinating agent instead of antimony(III) fluoride. ... 

The outcome of the reaction between 1,8-dilithionaphthalene and di-chlorophosphines RPCI2 is dependent on the nature of the R group at phosphorus. Thus, the reaction with phenyldichlorophosphine leads to the diphosphine... 

Several reports have appeared of the application of unusual organometallic reagents in phosphine synthesis. Treatment of 2-lithiopyridine with anhydrous zinc chloride results in the formation of a 2-pyridylzinc reagent which can be used to introduce the 2-pyridyl group at phosphorus in a controlled manner. Thus, e.g., in its reaction with phenyldichlorophosphine, the 2-pyridyl-(phenyl)chlorophosphine (15) is formed. This has then been converted via the phosphide route into a new class of binucleating ligands (16). The sterically crowded dichlorophosphine (17) (accessible from the reaction of phosphorus trichloride with lithium diphenyl(2-pyridyl)methanide) is converted into the thermally stable phosphirane (18) on treatment with calcium, strontium or barium cyclooctatetraenide.The reaction of phenyldichlorophosphine with the readily accessible titanacycle (19) affords a convenient route to the phosphetene (20). ... 

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