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Phosphonates arylphosphonates

Dialkyl arylphosphonates and alkenylphosphonates are prepared by the coupling of halides or triflates with the dialkyl phosphonate 783[64l-643]. [Pg.244]

The photo-Arbuzov rearrangement of allyl-, benzyl- and naphtylmethyl-phosphites (Scheme 13), first developed by Bentrude et al. [20], found applications in the preparation of phosphonates (70-90%) [38]. Arylphosphonates have been shown to act as protein tyrosine kinase inhibitors [39] or non-hy-drolyzable analogs of phosphorylated tyrosine residues [40]. [Pg.51]

Et or Bu) and the phosphonation of iodoaromatics with dialkyl phosphonates, although in this case with poorer yields (better results of the dialkyl arylphosphonates are obtained by photostimulation). Chemical oxidation (using AgNO -peroxodi-sulphate) and anodic oxidation of aromatics in the presence of trialkyl phosphites produces dialkyl arylphosphonates in good yields. The Cul-catalysed arylation of dialkyl (cyanomethyl)-phosphonates affords dialkyl (a-cyanobenzyl)phosphonates. ... [Pg.151]

Diethyl arylphosphonates were synthesized by reactions of diethyl phosphonate with aryl iodides or bromides containing electron-donor or electron-acceptor substituents in the aromatic ring in aqueous MeCN or neat H2O in the presence of Pd complexes with water-soluble ligands.34 For example, MeCN/H20 (1 mL), PhBr (8.2 mmol), and Ph2P(C6H4S03Na-m) (approximately 0.4 mmol) were successively... [Pg.176]

Obrycki, R. and Griffith, C.E., Phosphonic acids and esters. XIX. Syntheses of substituted phenyl- and arylphosphonates by the photoinitated arylation of trialkyl phosphites,. Org. Chem., 33, 632, 1968. [Pg.182]

The palladium-catalysed cross-coupling of aryl halides or vinyl halides with dialkyl phosphonates (31) to yield dialkyl arylphosphonates and dialkyl vinylphosphonates, respectively, was first reported by Hirao and co-workers 69 the halides used most frequently are bromides and the reaction is stereospecific with haloalkenes. Subsequently, analogous reactions of alkyl alkylphosphinates (32), alkyl arylphosphinates (32), alkyl phosphinates (33), and secondary phosphine oxides (34), replacing [P—H] bonds with [P—C] bonds to yield various phosphinates and tertiary phosphine oxides, have been developed (Figure 7.1). Alkyl phosphinates (33) may be mono- or diarylated as desired by the selection of appropriate conditions. Aiyl and vinyl triflates have also found limited... [Pg.189]

Reports on arylphosphonates include the synthesis and resolution of new racemic phosphonic acid methyl (213) and dimethyl esters (214) via cinchonium salts (Scheme 56). The absolute configuration of the phosphonic ester products was also established. [Pg.145]

Reports of examples of arylphosphonates include those of water-soluble phosphinic-polyphosphonic acids, e.g. 132, and the phosphonate 133 which when coupled to alcohols, to give e.g. 134, act as linkers to proteins in experiments intended to generate antibodies to catalyse cationic cyclisation reactions.Novel water-soluble phosphonate-substituted phthalocyanines have been prepared.The phosphonate esters 135 are insoluble in water but can be hydrolysed by hydrochloric acid to give the water-soluble phosphonic acids 136. Aromatic phosphonate-phosphines 137, and their air-stable complexes, have been obtained from the reaction of 4-halogeno-substituted phenylphosphonates with lithium diphenylphosphide. ... [Pg.116]

Moskva, V.V., Maikova, A.I., and Razumov, A.I., Phosphonic and phosphonous acid derivatives. Part 64. Reaction of phosphites and arylphosphonates with orthoacetic ester, Zh. Obshch. Khim., 39, 2451, 1969 J. Gen. Chem. (Engl. Transl.), 39, 2391, 1969. [Pg.243]

Aryl phosphonates. Phosphite anioo DMF. Arylphosphonate esters are obtained... [Pg.136]

Dialkyl arylphosphonates are also obtained from sodium dialkyl phosphites and aryl halides in the presence of Cu I in HMPTin a similar reaction, diethyl (l-cycloalkenyl)phosphonates with carbon rings having up to 12 atoms were prepared in 50—70% yields from the 1-cycloalkenyl chloride and the copper(i) adduct from triethyl phosphite. ... [Pg.111]

A novel route to the dialkyl arylphosphonates (34) involves the use of (l,2-propadiene)phosphonate anions with vinamidinium salts the yields vary from 5 to 83%. The use of 2-(dimethylamino)enones yields the phosphonic esters (35) in 48— 90% yields in a less-well exemplified series. ... [Pg.111]

New routes to substituted arylphosphonates (102) and (103) are available from the reactions of phosphonate carbanions with vinamidinium salts and P-dimethyl-amino enones, respectively. ... [Pg.240]

The stereochemistry of alkylation of chiral phosphorus-stabilised carbanions (138) has been investigated and shown to be highly sensitive to the nature of the nitrogen substituent. Phase-transfer catalysed alkylation of 2-(diethoxyphosphinyl)cyclohexanone (139) gives bothO-(140) and C-(141) alkylated products. The latter predominate when reactive, non-sterically demanding alkyl halides are used. a-Arylphosphonates (142) have been synthesised in good yields by the copper(l) salt-mediated arylation of phosphonate carbanions. Under similar conditions A-(2-iodophenyl)-substituted phosphonates provide benzoxazole-(143) and oxindole-(144) substituted phosphonates. [Pg.282]

It was shown that dialkyl arylphosphonates were prepared in good yield by the reaction of aryl iodides or bromides with dialkyl H-phosphonates in the presence of triethylamine and a catalytic amount of tetrakis(triphenylphosphine)palladium [368],... [Pg.214]

Aryl phosphonic esters are formed by reaction of triaryl phosphites with excess alcohol at 200°C (6.270). The corresponding acids can be obtained from these by hydrolysis. Arylphosphonic acids can be conveniently made from phosphorodipiperidic chloride and a lithium aryl The phosphonic dipiperidic amide so obtained is decomposed by water (6.271). [Pg.365]

Transesterification of a Phosphonate with a Diol. This method proceeds well in the case of 0,0-dialkyl hydrogen phosphonates (101) but less selectively with 0,0-dialkyl alkyl- or arylphosphonates. With 0,0-diaryl alkylphosphonates, ester exchange is an effective route to pol5uneric phosphonates (102-104) ... [Pg.5569]

A plausible formation path for dialkyl arylphosphonates is as follows. Palladium(O) species undergoes oxidative addition with aryl bromide to give the arylpalladium species, which reacts with dialkyl phosphite or phosphonate to give dialkyl arylphosphonate. [Pg.11]


See other pages where Phosphonates arylphosphonates is mentioned: [Pg.175]    [Pg.381]    [Pg.437]    [Pg.243]    [Pg.280]    [Pg.641]    [Pg.217]    [Pg.128]    [Pg.736]    [Pg.18]    [Pg.99]    [Pg.105]    [Pg.105]    [Pg.107]    [Pg.498]    [Pg.143]    [Pg.1141]    [Pg.506]    [Pg.300]    [Pg.271]    [Pg.32]    [Pg.377]    [Pg.378]    [Pg.380]    [Pg.381]   
See also in sourсe #XX -- [ Pg.348 , Pg.398 ]




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Arylphosphonates

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