Phosphonate synthesis

ARBUZOV MICHAELIS Phosphonale Synihesis Ni catalyzed phosphonate synthesis from phosphites and aryl halides Reaction of alkyl halides with phosphites proceeds without nickel salts... 

Oleksyszyn, J., Subotkowska, L., and Mastalerz, P., Diphenyl 1-aminoalkane-phosphonates, Synthesis, 985, 1979. 

Phosphonate synthesis from the reaction of aikyi haiides with phosphites. 

Phenyl-N-(phenylmethylene)-l-propen-1-amine 1-Propen-1-amine, 2-phenyl-N-(phenylmethylene)-, (64244-34-4), 65, 119 (E)-3-[(E)-3-Phenyl-2-propenoxy]acry1lc acid, (88083-18-5), 66, 30, 31, 36 ( )-trans-2-(PHENYLSULFONYL)-3-PHENYLOXAZIRIDINE, 66, 203, 204 1-Phenyl-1-trimethylsiloxyethylene Silane, tnmethyl[(1-phenylvinyl)oxy]-, Silane, trimethyl[(l-phenylethenyl)oxy]- (13735-81-4), 65, 6 Phosphonate synthesis, 66, 194... 

ALPER Carbonylalion 2 AMADORI Glucosamine rearrangement 3 ANGELl - RIMINI Hydroxarrw acid synthesis 4 ARBUZOV - MICHAELIS Phosphonate synthesis 5... 

Nakano, M., Okamoto, Y., and Sakurai, H., Preparation of dialkyl 2-cyano-2-(trimethylsilyl)ethane-phosphonates. Synthesis, 915, 1982. 

Balczewski, P, and Mikolajczyk, M., Free radical reaction of a-haloalkylphosphonates with alkenes and alkynes. A new approach to modified phosphonates. Synthesis, 392, 1995. 

Schrader, T., and Steglich, W., Phosphorus analogs of amino acids. Part 4. Syntheses of unusual 1-aminophosphonic acids via Diels-Alder reactions of diethyl (7V-acyliminomethyl)phosphonates, Synthesis, 1153, 1990. 

Burgos-Lepley, C.E., Mizsak. S.A., Nugent, R.A., and Johnson, R.A., Tetraalkyl oxira-nylidenebis(phosphonates). Synthesis and reactions with nucleophiles, J. Org. Chem., 58,4159, 1993. 

Drescher, M., Ohler, E., and Zbiral, E., A convenient approach to dialkyl heteroarylmethylphospho-nates and [alkylthio(heteroaryl)methyl]phosphonates. Synthesis of imidazo[l,2-a]pyridine, imi-dazo[l,2-fii]pyrimidine, indohzine and thiazole derivatives. Synthesis, 362, 1991. 

Sawamnra, M., Hamashima, H., and Ito, Y., Rhodium-catalyzed enantioselective Michael addition of (l-cyanoethyl)phosphonate. Synthesis of optically active phosphonic acid derivatives with phosphorussubstituted quaternary asymmetric carbon center, Bull. Chem. Soc. Jpn., 73, 2559, 2000. 

Goumain, S., Jubault, P, Feasson, C., and Collignon, N, A new and efficient electrosynthesis of 2-substituted l,l-cyclopropanediylhw(phosphonates). Synthesis, 1903, 1999,... 

Rudisill, D.E., and Whitten, J.P., Synthesis of (7 i-4-oxo-5-phosphononorvalinc, an JV-methyl-D-aspar-tic acid receptor selective P-keto phosphonate. Synthesis. 851. 1994. 

Rosini, G., Baccolini, G., and Cacchi, S., Reactions of 1-oxoalkanephosphonate tosylhydrazones with sodium borohydride. New synthesis of dimethyl alkanephosphonates and dimethyl 1-diazoalkane-phosphonates. Synthesis, 44, 1975. 

Ohler, E., and Kanzler, S., (2//-A/.irin-2-yl)melhyl]phosphonates. Synthesis from allylic a- and y-hydroxyphosphonates and apphcation to diastereoselective formation of substituted [(azirin-2-yl)methyl]phosphonates, Liebigs Ann. Chem.. 867, 1994. 

Goumain. S., Jubault, P., Feasson. C.. and Quirion, J.-C., First synthesis of a-fluorinated cyclopro-pylphosphonates using magnesium electrochemical activation, Tetrahedron Lett.. 40, 8099, 1999. Goumain, S., Jubault, P., Feasson, C., and Collignon, N., A new and efficient electrosynthesis of 2-substituted l,l-cyclopropanediylbis(phosphonates). Synthesis, 1903, 1999. 

Nucleophilic Reactions.—Attack on Saturated Carbon. The Arbusov reaction has been widely used in phosphonate synthesis. This has been extended to the preparation of the unsymmetrical diphosphine ligand (2) through reaction of... 

The methodology has been resurrected very recently in the H-phosphonate variant. An attempt by Adamo et al. [326] to use a chlorosulfonated polystyrene resin for activation of the nucleoside H-phosphonate monoesters was not particularly impressive, but the corresponding chlorocarbonylated polystyrene performed well, permitting the synthesis of up to a hexanucleotide. Similar results were reported by Mohe et al. [327] for the dinucleoside H-phosphonate synthesis promoted by a phosphorochloridate supported on polystyrene. 

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