Phase Transfer Catalysis in Phosphorus Chemistry

REFERENCES

• International Union of Pure and Applied Chemistry. Compendium of Chemical Terminology, 2nd ed. McNaught, A.D.; Wilkinson, A., Comps.; Blackwell Scientific Publications: Oxford, 1997. XML on-line corrected version http://goldbook.iupac.org (http://goldbook.iupac.org)
   Google Scholar
• Starks , C.M. 1971 . Phase-Transfer Catalysis. I. Heterogeneous Reactions Involving Anion Transfer by Quaternary Ammonium and Phosphonium Salts . J. Am. Chem. Soc. , 93 ( 1 ) : 195 – 199 .
   Web of Science ®Google Scholar
• Dehmlow , E.V. and Dehmlow , S.S. 1993 . Phase Transfer Catalysis , 3rd , Weinheim, , Germany : VCH .
   Google Scholar
• Starks , C.M. , Liotta , C.L. and Halpern , M.E. 1994 . Phase-Transfer Catalysis , New York : Chapman & Hall .
   Google Scholar
• Sasson , Y. and Neumann , R. , eds. 1997 . Handbook of Phase-Transfer Catalysis , London : Blackie Academic & Professional .
   Google Scholar
• Halpern , M.E. , ed. 1997 . Phase-Transfer Catalysis , Washington, DC : ACS Symposium Series 659; American Chemical Society .
   Google Scholar
• Shioiri , T. 1997 . “ Chiral phase transfer catalysis ” . In Handbook of Phase-Transfer Catalysis, Ch. 14 , Edited by: Sasson , Y. and Neumann , R. 462 – 479 . London : Blackie Academic & Professional .
   Google Scholar
• Naik , S.D. and Doraiswamy , L.K. 1998 . Phase Transfer Catalysis: Chemistry and Engineering . AIChE J. , 44 ( 3 ) : 612 – 646 .
   Web of Science ®Google Scholar
• Zwierzak , A. 1976 . Phase-Transfer-Catalysed Phosphorylation of Alcohols in a Two-Phase System . Synthesis , : 305 – 306 .
   Web of Science ®Google Scholar
• Ilia , G. , Popa , A. , Iliescu , S. , Bora , A. , Dehelean , G. and Pascariu , A. 2003 . Synthesis of Mixed Alkylphosphites and Alkylphosphates . Phosphorus, Sulfur, and Silicon and the Related Elements , 178 ( 7 ) : 1513 – 1519 .
   Web of Science ®Google Scholar
• Ilia , G. , Kurunczi , L. , Dehelean , G. , Iliescu , S. and Macarie , L. 1999 . Synthesis of Some Mixed Dialkyl Phosphites and Their Use as Forerunners for Potential Chiral Phosphates . Phosphorus, Sulfur, and Silicon and the Related Elements , 147 ( 1 ) : 191
   Google Scholar
• Ilia , G. , Iliescu , S. , Dehelean , G. , Popa , A. , Păcureanu , L. , Macarie , L. and Pascariu , A. 2002 . Synthesis of Mixed Dialkylphosphates by Phase Transfer Catalysis Method . Phosphorus, Sulfur, and Silicon and the Related Elements , 177 ( 8,9 ) : 2049 – 2050 .
   Web of Science ®Google Scholar
• Ramirez , F. and Marecek , J.F. 1976 . Acetate Ion Catalysis of Phosphorylation in Aprotic Solvents . Tetrahedron Lett. , 17 ( 42 ) : 3791 – 3794 .
   Google Scholar
• Ding , Y.X. and Zhou , S.F. 1994 . A Novel and Facile Route to the Phosphorylation of Carbohydrates by the L-S PTC Modified Procedure of the Atherton-Todd Reaction . Phosphorus, Sulfur, and Silicon and the Related Elements , 92 ( 1–4 ) : 219 – 223 .
   Web of Science ®Google Scholar
• Anisimova , A.A. , Martynova , E.A. , Pikalev , L.P. and Yacovlev , A. 2000 . Reaction of Dialkylhydrogen Phosphites with 2,2-Dichlorocyclopropylcarbinol . Russ. J. Gen. Chem. , 70 ( 12 ) : 1817 – 1818 .
   Google Scholar
• Szulc , Z.M. , Obeid , L.M. , Hannun , Y.A. and Bielawska , A. 2007 . Highly Efficient and Regioselective Phosphorylation of Sphingolipids by Phase-Transfer Catalysis . Pol. J. Chem. , 81 ( 19 ) : 1899 – 1909 .
   Google Scholar
• Krishnakumar , V.K. and Sharma , M.M. 1985 . Kinetics of Formation of Triphenyl Phosphate: Phase-Transfer Catalysis in a Liquid-Liquid System . Ind. Eng. Chem. Process Des. Dev. , 24 ( 4 ) : 1293 – 1297 .
   Web of Science ®Google Scholar
• Krishnakumar , V.K. 1984 . Synthesis of Triaryl Phosphates Catalysed by Polyethylene Glycols in a Two-Phase System: Phase Transfer Catalysis . Synthetic Comm. , 14 ( 2 ) : 189 – 196 .
   Web of Science ®Google Scholar
• Asai , S. , Nakamura , H. , Tanabe , M. and Sakamoto , K. 1994 . Synthesis of Triphenyl Phosphate and Benzyl Benzoate with Phase Transfer Catalyst in Heterogeneous Liquid-Liquid Reaction System . Ind. Eng. Chem. Res. , 33 ( 7 ) : 1687 – 1691 .
   Web of Science ®Google Scholar
• Process for the Production of Phosphoric Acid Triesters . U.S. Patent 4267127 . 1981 .
   Google Scholar
• Process for the Production of Neutral Phosphoric Acid Esters . U.S. Patent 4290977 . 1981 .
   Google Scholar
• Process for the Preparation of Neutral Phosphoric Acid Esters by the Interface Method and Compounds Produced by This Process . German Patent DE 2833342 . 1980 .
   Google Scholar
• Process for the Preparation of Phosphoric Esters and Thiophosphoric Esters . German Patent DE2944778 . 1980 .
   Google Scholar
• Process for the Preparation of Phosphoric Esters and Thiophosphoric Esters . U.S. Patent 4256672 . 1981 .
   Google Scholar
• Talley , J.J. and Berman , C.B. 1987 . Phase-Transfer-Catalyzed Preparation of Triaryl Phosphorothionates . J. Chem. Eng. Data , 32 ( 2 ) : 279 – 280 .
   Web of Science ®Google Scholar
• Dehelean , G. , Iliescu , S. , Ilia , G. , Popa , A. , Macarie , L. and Păcureanu , L. 2001 . Phase-Transfer Catalysis (PTC) in Organophosphorus Compounds Synthesis 1. Liquid-Liquid PTC Synthesis of Phosphorodichloridothioic Acid o-Aryl Esters . Rev. Roum. Chim. , 46 ( 1 ) : 31 – 35 .
   Google Scholar
• Dehelean , G. , Ilia , G. , Iliescu , S. , Popa , A. , Macarie , L. and Pascariu , A. 2002 . The Influence of the Molar Ratio SPCl3: Phenol on the Formation of the Disubstituted Secondary Products in the Liquid-Liquid PTC Synthesis of Aryltiophosphoric Acid Diclorides . Phosphorus, Sulfur, and Silicon and the Related Elements , 177 ( 8–9 ) : 2193 – 2194 .
   Web of Science ®Google Scholar
• Dehelean , Gh. , Iliescu , S. , Ilia , Gh. and Popa , A. 2003 . Macarie, L;. Păcureanu, L. Phase-Transfer Catalysis (PTC) in Organophosphorus Compounds Synthesis 1. PTC Synthesis, in Liquid-Liquid, System of Phosphorodichloridothioic Acid o-Aryl Esters Part b. Study of the Influence of Molar Ratio of Reactants on Yield and Purity of Phosphorodichloridothioic Acid o-Aryl Esters . Rev. Roum. Chim. , 48 ( 2 ) : 133 – 136 .
   Web of Science ®Google Scholar
• Ridgway , R.W. , Greenside , H.S. and Freedman , H.H. 1976 . Cocatalysis of Phenolate Phosphorylation in Biphasic Media . J. Am. Chem. Soc. , 98 ( 7 ) : 1979 – 1980 .
   Web of Science ®Google Scholar
• Process for Preparing Phosphorothioates and Phenylphosponothioates . U.S. Patent 3972887 . 1976 .
   Google Scholar
• Genkina , G.K. , Shipov , A.E. , Mastryukova , T.A. and Kabacknik , M. 1996 . Synthesis of Unsymmetrical Triaryl Phosphates under Phase Transfer Catalysis . Russ. J. Gen. Chem. , 66 ( 11 ) : 1742 – 1744 .
   Google Scholar
• Tang , R. and Gou , C. 2005 . The Synthesis and Evaluation of Novel Aryl-Substituted Dithioimidophosphonates as an Extractant for Metals . Phosphorus, Sulfur, and Silicon and the Related Elements , 180 ( 12 ) : 2725 – 2731 .
   Web of Science ®Google Scholar
• White , R. J. , Margolis , P.S. , Trias , J. and Yuan , Z. 2003 . Targeting metalloenzymes: a strategy that works . Curr. Opin. Pharmacol , 3 ( 5 ) : 502 – 506 .
   PubMed Web of Science ®Google Scholar
• Ravikumar , V.T. and Ross , B. 2004 . 2-Chlorophenyl Phosphorodichloridothioate . Organic Syntheses Collective Volumes , 10 : 226
   Google Scholar
• Process for Preparing Phosphorothioates and Phenylphosphonothioates . U.S. Patent 3917621 . 1975 .
   Google Scholar
• Process for Preparing Phosphorothioates and Phenylphosphonothioates . U.S. Patent 3907815 . 1975 .
   Google Scholar
• Giorgi-Renaut , S. , Renault , J. and Bukovec , Z. 1984 . Phase Transfer Catalysis: A Convenient Synthesis of o,o-Diethyl o-(4-quinolinyl) Phosphorothioates . Synthesis , : 491 – 492 .
   Web of Science ®Google Scholar
• Byrne , L.T. , Harrowfield , J.M. , Hockless , D.C.R. , Peachey , B.J. , Skelton , B.W. and White , A.H. 1993 . Calixarene Phosphorylation: Cation Control of Reaction Pathways . Austr. J. Chem. , 46 ( 11 ) : 1673 – 1683 .
   Web of Science ®Google Scholar
• Process for Preparing Phosphorothioates and Phenylphosphonothioates . U.S. Patent 4007197 . 1977 .
   Google Scholar
• Process for the Production of Thiophosphoric Acid Esters . U.S. Patent 4326059 . 1982 .
   Google Scholar
• Halpen , M. 2005 . Achieving Competitive Advantage Using Phase-Transfer Catalysis in Generic Pharmaceuticals and Agrochemicals . Industrial Phase-Transfer Catalysis , 18 : 1 – 16 .
   Google Scholar
• Zwierzak , A. 1975 . Phase-Transfer-Catalysed Phosphorylation of Amines in an Aqueous System . Synthesis , : 507 – 508 .
   Web of Science ®Google Scholar
• Weber , W.P. and Gokel , G.W. 1972 . An Improved Procedure for the Hofmann Carbylamine Synthesis of Isonitriles . Tetrahedron Lett. , 13 ( 17 ) : 1637 – 1640 .
   Google Scholar
• Zwierzak , A. and Brylikowska , J. 1975 . N,N-Dihalophosphoramides; IX. Dialkyl N-Alkoxy-N-Chlorophosphoramidates . Synthesis , : 712 – 713 .
   Web of Science ®Google Scholar
• Zwierzak , A. and Suleswska , A. 1976 . Solid-Liquid Phase-Transfer-Catalysed Phosphorylation of Hydrazine. Preparation of Dialkyl Phosphorohydrazidates and N,N′-bis[Dialkoxyphosphoryl]hydrazines . Synthesis , : 835 – 836 .
   Web of Science ®Google Scholar
• Zwierzak , A. and Osowska , K. 1984 . A Convenient Method for the Protection of Amino Groups as Diethyl Phosphoramidates . Synthesis , : 223
   Web of Science ®Google Scholar
• Lukanov , L.K. , Venkov , A.P. and Mollov , N.M. 1985 . A New Approach to the Atherton-Todd Reaction . Synthesis , : 971 – 972 .
   Web of Science ®Google Scholar
• Lukanov , L.K. , Venkov , A.P. and Mollov , N.M. 1986 . The Application of Phase-Transfer Catalyzed Version of Atherton-Todd Reaction to Sulfonamides . Synthetic Comm. , 16 ( 7 ) : 767 – 773 .
   Web of Science ®Google Scholar
• Ma , X.-B. and Zhao , Y.-F. 1992 . A Convenient Synthesis of N-Phosphoryldipeptide Acids by Direct Phosphorylation . Synthesis , : 759 – 760 .
   Google Scholar
• Zhang , J.C. , Cao , S.X. , Yang , X.L. and Zhao , Y.F. 2004 . A Facile Synthesis of N-Phosphoryl Amino Acids Containing Hydroxy Group . Chin. Chem. Lett. , 15 ( 6 ) : 646 – 648 .
   Web of Science ®Google Scholar
• Chellini , A. , Pagliarin , R. , Giovenzana , G.B. , Palmisano , G. and Sisti , M. 2000 . Diethoxyphosphoryl as a Protecting-Activating Group in the Synthesis of Polyazacyclophanes . Helv. Chim. Acta , 83 ( 5 ) : 793 – 800 .
   Web of Science ®Google Scholar
• Kem , K.M. , Nguyen , N.V. and Cross , D.J. 1981 . Phase-Transfer-Catalyzed Michaelis-Becker Reaction . J. Org. Chem. , 46 ( 25 ) : 5188 – 6192 .
   Web of Science ®Google Scholar
• Ye , W. and Liao , X. 1985 . Synthesis of Dialkyl Alkoxycarbonylmethanephosphonates (Alkyl Dialkoxyphosphinylacetates) Using Phase-Transfer Catalysis . Synthesis , : 986 – 987 .
   Web of Science ®Google Scholar
• Makosza , M. and Wojciechowski , K. 1984 . Synthesis of Phosphonic Acid Esters in a Solid-Liquid Catalytic Two-Phase System . Bull. Pol. Acad. Sci. Chem. , 32 ( 2 ) : 175 – 183 .
   Google Scholar
• Fedorynski , M. , Wojciechowski , K. , Matacz , Z. and Makosza , M. 1978 . Reactions of Organic Anions. 86. Sodium and Potassium Carbonates: Efficient Strong Bases in Solid-Liquid Two-Phase Systems . J. Org. Chem. , 43 ( 24 ) : 4682 – 4684 .
   Web of Science ®Google Scholar
• Phosphonic Acid Esters . Polish Patent 105428 . 1980 .
   Google Scholar
• Fakhraian , H. and Mirzaei , A. 2006 . Phase-Transfer-Catalyzed Michaelis-Becker Synthesis of Dialkyl Methyl Phosphonates . Phosphorus, Sulfur, and Silicon and the Related Elements , 181 ( 3 ) : 511 – 518 .
   Web of Science ®Google Scholar
• Platonov , A.Yu. , Sivakov , A.A. , Chistokletov , K.N. and Maiorova , E.D. 1999 . Transformations of Electrophilic Reagents in a Diethyl Phosphite-Potassium Carbonate-Ethanol System . Russ. Chem. Bull. , 48 ( 2 ) : 367 – 370 .
   Web of Science ®Google Scholar
• Cohen , Ri.J. , Fox , D.L. , Eubank , J.F. and Salvatore , R.N. 2003 . Mild and Efficient Cs2CO3-Promoted Synthesis of Phosphonates . Tetrahedron Lett. , 44 ( 47 ) : 8617 – 8621 .
   Web of Science ®Google Scholar
• Kabachnik , M.M. , Solntseva , M.D. and Beletskaya , L.P. 1997 . Palladium-Catalyzed Arylation of Hydrophosphoryl Compounds under Conditions of Phase Transfer Catalysis . Russ. Chem. Bull. , 46 ( 8 ) : 1491
   Web of Science ®Google Scholar
• Nikolova , R. , Bojilova , A. and Rodios , N.A. 1998 . Reaction of 3-Bromobenzyl and 3-Bromoacetyl Coumarin with Phosphites. Synthesis of Some New Phosphonates and Phosphates in the Coumarin Series . Tetrahedron , 54 ( 47 ) : 14407 – 14420 .
   Web of Science ®Google Scholar
• Yoshikawa , H. , Shono , T. and Eto , M. 1984 . A Facile Synthesis and Insecticidal Activity of Optically Active Phenylphosphonothiolates . J. Pestic. Sci. , 9 ( 3 ) : 455 – 462 .
   Web of Science ®Google Scholar
• Juan , C. , Feng , H. and Lin , Q. 1989 . Studies on Organophosphorus Compounds XXXIII. Chemoselective Phase-Transfer Catalytic S-Alkylation of Dialkyl/Diarylthiophosphinic Acids; a New Facile Route to S-Alkyl Dialkyl/Diarylthiophosphinates . Synthesis , : 48 – 49 .
   Web of Science ®Google Scholar
• Dehelean , G. , Ilia , G. , Iliescu , S. , Popa , A. , Macarie , L. and Păcureanu , L. 2002 . Synthesis of Some α-Hydroxphosphonates under Phase Transfer Catalysis Conditions . Rev. Chim. , 53 ( 1 ) : 44 – 47 .
   Web of Science ®Google Scholar
• Villemin , D. and Racha , R. 1986 . Anionic activation of diethylphosphate by potassium fluoride deposited on alumina. Synthesis of Functionalized phosphonates . Tetrahedron Lett. , 27 ( 16 ) : 1789 – 1790 . (in French)
   Web of Science ®Google Scholar
• Petnehazy , I. , Jaszay , Z.M. and Tőke , L. 1996 . Phosphite Addition to Carbonyl Group and Phosphoryl Migration under Phase Transfer Catalytic Circumstances . Phosphorus, Sulfur, and Silicon and the Related Elements , 109 ( 1–4 ) : 421 – 424 .
   Web of Science ®Google Scholar
• Jaszay , Z.M. , Petnehazy , I. , Szabo , A. , Bako , P. , Clementis , G. and Toke , L. 1999 . Enantioselective Synthesis of α-Alkoxy-Phosphonates by Chiral Phase Transfer Catalysis . Phosphorus, Sulfur, and Silicon and the Related Elements , 147 ( 1 ) : 135 – 135 .
   Google Scholar
• Kabachnik , M.M. , Ternovskaya , T.N. , Zobnina , E.V. and Beletskaya , I.P. 2002 . Synthesis of α-Aminophosphonates under Conditions of Phase-Transfer Catalysis . Russ. J. Org. Chem. , 38 ( 4 ) : 484 – 486 .
   Web of Science ®Google Scholar
• Fini , F. , Micheletti , G. , Bernardi , L. , Pettersen , D. , Fochi , M. and Ricci , A. 2008 . An Easy Entry to Optically Active α-Amino Phosphonic Acid Derivatives Using Phase Transfer Catalysis (PTC) . Chem. Comm. , : 4345 – 4347 .
   PubMed Web of Science ®Google Scholar
• Roos , G.H.P. and Balasubramaniam , S. 1998 . Synthesis of α-Amino Phosphonates under Diastereocontrol by Imidazolidin-2-one Auxiliaries . Synthetic Comm. , 28 ( 20 ) : 3877 – 3884 .
   Web of Science ®Google Scholar
• Kluba , M. and Zwierzak , A. 1978 . Alkylation of Tetra-n-Butylaminium Alkyl Hydrogen phosphites. A New Route to Mixed Dialkyl Phosphites . Synthesis , : 134 – 136 .
   Web of Science ®Google Scholar
• Bauman , R.A. 1974 . The Preparation of Mixed Dialkyl Phosphates . Synthesis , : 870 – 871 .
   Web of Science ®Google Scholar
• Gazaliev , A.M. , Fazylov , S.D. , Balitskii , S.N. and Kasenov , R.Z. 1992 . Synthesis of Organophosphorus Derivatives of Lupinine and Solasodine and Investigation of Their Cholinergic Activities . Chem. Nat. Comp. , 28 ( 5 ) : 472 – 473 .
   Google Scholar
• Gusarova , N.K. , Trofimov , B.A. , Malysheva , S.F. , Rakhmatulina , T.N. , Vyalykh , E.P. and Voronkov , M.G. 1989 . Reaction of Red Phosphorus with Benzyl Halides in a Superbase System . Russ. Chem. Bull. , 38 ( 2 ) : 430
   Web of Science ®Google Scholar
• Malysheva , S.F. , Gusarova , N.K. , Rakhmatulina , T.N. , Kazantseva , T.I. , Dmitriev , V.I. and Trofimov , B.A. 1989 . Tris(2-phenylethyl)phosphine oxide from red phosphorus and styrene . Russ. Chem. Bull. , 38 ( 7 ) : 1569
   Web of Science ®Google Scholar
• Trofimov , B.A. , Gusarova , N.K. , Malysheva , S.F. , Vyalykh , E. P. , Rakhmatulina , T.N. and Voronkov , M.G. 1988 . Synthesis of Tristyrylphosphine from Red Phosphorus and Phenylacetylene in a Superbase System . Russ. Chem. Bull. , 37 ( 6 ) : 1284
   Web of Science ®Google Scholar
• Trofimov , B.A. , Gusarova , N.K. , Shaikhudinova , S.I. , Rakhmatulina , T.N. , Malysheva , S.F. , Oparina , L.A. , Dmitriev , V.I. and Voronkov , M.G. 1990 . Synthesis of tris(2,2-Dialkoxyethyl)phosphine Oxides from Red Phosphorus and 1,1-Dialkoxy-2-Bromoethanes in Superbase Systems . Russ. Chem. Bull. , 39 ( 12 ) : 2606 – 2607 .
   Web of Science ®Google Scholar
• Trofimov , B.A. , Gusarova , N.K. , Malysheva , S.F. , Kuimov , V.A. , Sukhov , B.G. , Shaikhudinova , S.I. , Tarasova , N.P. , Smetannikov , Yu.V. , Sinyashin , O.G. , Budnikova , Yu.G. , Kazantseva , T.I. and Smirnov , V.I. 2005 . Reactions of Elemental Phosphorus with Electrophiles in Super Basic Systems: XVII.1 Phosphorylation of Arylalkenes with Active Modifications of Elemental Phosphorus . Russ. J. Gen. Chem. , 75 ( 9 ) : 1367 – 1372 .
   Web of Science ®Google Scholar
• Gusarova , N.K. , Arbuzova , S.N. , Bogdanova , M.V. , Pavlov , D.V. , Komarova , T.N. and Trofimov , B.A. 2005 . First Example of Microwave Activation of Elementary Phosphorus in the Reaction with 2-Vinylpyridine . Russ. J. Gen. Chem. , 75 ( 11 ) : 1844 – 1845 .
   Web of Science ®Google Scholar
• Gusarova , N.K. , Malysheva , S.F. , Arbuzova , S.N. and Trofimov , B.A. 1998 . Synthesis of Organic Phosphines and Phosphine Oxides from Elemental Phosphorus and Phosphine in the Presence of Strong Bases . Russ. Chem. Bull. , 47 ( 9 ) : 1645 – 1652 .
   Web of Science ®Google Scholar
• Trofimov , B. , Gusarova , N. and Brandsma , L. 1996 . Generation of Phosphide Anions from Phosphorus Red and Phosphine in Strongly Basic Systems to Form Organylphosphines and -Oxides . Phosphorus, Sulfur, and Silicon and the Related Elements , 109 ( 1–4 ) : 601 – 604 .
   Web of Science ®Google Scholar
• Rabinovitz , M. , Cohen , Y. and Halpern , M. 1986 . Durch Reactions under Phase Transfer Catalysis by Hydroxyl Ions: Mechanism and Applications . Angew. Chem. , 98 ( 11 ) : 958 – 968 . (in German)
   Google Scholar
• Weferling , N. , Sicken , M. and Hoerold , S. 2002 . Formation of Methyl-Phosphonous Acid by Alkylation of Yellow Phosphorus . Phosphorus, Sulfur, and Silicon and the Related Elements , 177 ( 6–7 ) : 1757 – 1761 .
   Web of Science ®Google Scholar
• Shaikhutdinova , S.I. , Kazantseva , T.I. , Gusarova , N.K. , Dmitriev , V.I. and Trofimov , B.A. 2001 . Reactions of Elemental Phosphorus and Phosphine with Electrophiles in Superbasic Media: XI.1 Phosphorylation of 4-Methoxybenzyl Chloride with Elemental Phosphorus and Phosphine . Russ. J. Gen. Chem. , 71 ( 1 ) : 58 – 60 .
   Web of Science ®Google Scholar
• Gusarova , N.K. , Shaikhutdinova , S.I. , Kazantseva , T.I. , Malysheva , S.F. , Sukhov , B.G. , Belogorlova , N.A. , Dmitriev , V.I. and Trofimov , B.A. 2002 . Reactions of Elemental Phosphorus and Phosphine with Electrophiles in Superbasic Systems: XIV.1 Phosphorylation of 2-Vinylnaphthalene with Elemental Phosphorus and Phosphines in the KOH-DMSO System . Russ. J. Gen. Chem. , 72 ( 3 ) : 371 – 375 .
   Web of Science ®Google Scholar
• Sukhov , B.G. , Malysheva , S.F. , Kuimov , V.A. , Smetannikov , Yu.V. , Tarasova , N.P. , Lupanov , A.N. , Gusarova , N.K. and Trofimov , B.A. 2004 . Reaction of Activated Red Phosphorus with Allyl Bromide under Phase-Transfer Catalysis . Russ. J. Gen. Chem. , 74 ( 7 ) : 1128 – 1129 .
   Web of Science ®Google Scholar
• Singh , R.K. 1986 . Alkylation Studies; Part II: Bis-Alkylation of Diethyl Cyanomethanephosphonate . Synthesis , : 762
   Web of Science ®Google Scholar
• Ruder , S.M. and Kulkarni , V.R. 1993 . Phase Transfer Catalyzed Alkylation of 2-(Diethoxyphosphinyl)Cyclohexanone . Synthesis , : 945 – 947 .
   Web of Science ®Google Scholar
• Blanchard , J. , Callignon , N. , Savignac , P. and Normant , H. 1975 . C-alkylation of Cyanomethanephosphonic Tetramethyldiamides Using Phase-Transfer Catalysis . Synthesis , : 655 – 656 .
   Web of Science ®Google Scholar
• Makosza , M. 1968 . Reactions of Organic Anions—IX: Competitive Alkylation of Acetonitrile Derivatives . Tetrahedron , 24 ( 1 ) : 175 – 183 .
   Web of Science ®Google Scholar
• Zwierzak , A. and Podstawezynska , I. 1977 . Alkylation of Diphenylphosphinamide by Phase Transfer Catalysis—A New Synthesis of Primary and Secondary Amines . Angew. Chem. , 89 ( 10 ) : 737 – 738 . (in German)
   Google Scholar
• Yuan , C. , Cui , S. , Wang , G. , Feng , H. , Chen , D. , Li , C. , Ding , Y. and Maier , L. 1992 . Studies on Organophosphorus Compounds, 53: A New Procedure for the Synthesis of 1-Alkyl or 1-Aryl-1-hydroxy-2-nitroethylphoshonates under PTC Conditions . Synthesis , : 258 – 260 .
   Web of Science ®Google Scholar
• Yuan , C. and Chen , S. 1992 . Studies on Organophosphorus Compounds; LXIII. A New and Facile Synthetic Route to Protected Phosphonodipeptides: A Backbone for the Formation of Oligophosphonopeptides . Synthesis , : 1124 – 1128 .
   Web of Science ®Google Scholar
• Vlassa , M. , Kezdi , M. , Fensan , I. and Bogdan , M. 1986 . Phase Transfer Alkylation of 2-Arylsulfonyl-amido-2-thiono-5,5-dimethyl-1,3,2-dioxaphosphorinanes with Dialkylsulphates . J. Prakt. Chem. , 328 ( 3 ) : 465 – 468 .
   Google Scholar
• Penz , G. and Zbiral , E. 1985 . Synthesis of (3-Oxo-2-tosyloxy-1-alkenyl) phosphonic acid dialkylester—Synton for (heteroarylmethyl)-phosphonates and 3-oxophosphonates 2-Substituted . Chem. Ber. , 118 ( 10 ) : 4131 – 4143 . (in German)
   Google Scholar
• Mastryukova , T. , Odinets , I. , Antipin , M. , Kalyanova , R. , Artyushin , O. , Matveeva , A. and Kabachnik , M. 1996 . Acylation of Phosphorus Substituted Ch-Acids under Phase Transfer Catalysis Conditions . Phosphorus, Sulfur, and Silicon and the Related Elements , 109 ( 1–4 ) : 577 – 580 .
   Web of Science ®Google Scholar
• Lazrek , H.B. , Rochdi , A. , Khaider , H. , Barascut , J.-L. , Imbach , J.-L. , Balzarini , J. , Witvrouw , M. , Pannecouque , C. and De Clercq , E. 1998 . Synthesis of (Z) and (E) α-Alkenyl Phosphonic Acid Derivatives of Purines and Pyrimidines . Tetrahedron , 54 ( 15 ) : 3807 – 3816 .
   Web of Science ®Google Scholar
• Rochdi , A. , Taourirte , M. , Lazrek , H.B. , Barascut , J.L. and Imbach , J.L. 2000 . Synthesis of New bis-Alkylated Phosphono Alkenyl Acyclonucleosides: (Z) and (E)-Diethyl-2-(3-alkyl pyrimidin-1-yl)ethylen-1-yl Phosphonate . Molecules , 5 ( 10 ) : 1139 – 1145 .
   Web of Science ®Google Scholar
• Ma , X. , Fu , X. , Li , L. and Chen , J. 2001 . Synthesis of the New Type of Water-Soluble Ligand N,N-Bis-(Diphenylphosphinomethyl)-2-Aminoethylphosphonic Acid (PhPCH2)2N-CH2CH2PO3H2 and Its Sodium Salt . Molecules , 6 ( 4 ) : 390 – 395 .
   Web of Science ®Google Scholar
• Kossev , K. , Troev , K. and Roundhill , D.M. 1993 . Synthesis of Dialkyl 1,2-Epoxyphosphonates under Phase-Transfer Catalyst Conditions . Phosphorus, Sulfur, and Silicon and the Related Elements , 83 ( 1–4 ) : 1 – 7 .
   Web of Science ®Google Scholar
• Deschamp , R. , Ricard , L. and Mathey , F. 1994 . Toward Polyphospholes: Synthesis and Structure of an α-Linked Quaterphosphole . Angew. Chem. Int. Ed. , 33 ( 11 ) : 1158 – 1161 .
   Web of Science ®Google Scholar
• Shipov , A.E. , Genkina , G.K. , Artyushin , O.I. , Volkova , R.I. , Makhayeva , G.F. , Roslavtseva , S.A. , Rosengart , E.V. , Kagan , Yu.S. , Guschin , B.E. , Mastryukova , T.A. and Kabachnik , M.I. 1996 . Synthesis, Biological Activity and Mechanism of Action of 1,3,2-Oxazaphosphorinane Derivatives . Phosphorus, Sulfur, and Silicon and the Related Elements , 109 ( 1–4 ) : 357 – 360 .
   Web of Science ®Google Scholar
• Keglevich , G. and Toke , L. 1996 . Uyszaszy, K.; Szollosy, A. Synthesis of Functionalized p-Heterocycles Including Phosphine-Borane Complexes . Phosphorus, Sulfur, and Silicon and the Related Elements , 109 ( 1–4 ) : 457 – 460 .
   Web of Science ®Google Scholar
• Gajda , T. and Zwierzak , A. 1976 . Phase-Transfer-Catalysed Halogenation of di-tert-butyl Phosphite. Preparation of di-tert-butyl Phosphorohalidates . Synthesis , 243
   Google Scholar
• Process for Preparing Phosphonic-Acid Dichlorides . German Patent DE3541627 . 1987 .
   Google Scholar
• Process for Preparing Alkyl or Arylthiophosphonic-Acid Chlorides . European Patent EP71783 . 1984 .
   Google Scholar
• Process for the Preparation of Phosphorothioic Dichlorides . European Patent EP283073 . 1993 .
   Google Scholar
• Abdou , W.M. , Salem , M.A.I. and Barghash , R.F. 2003 . The Reactions of Triphenylphosphine Alkylenes with 3(2-Thienyl)acrylonitriles . Phosphorus, Sulfur, and Silicon and the Related Elements , 178 ( 1 ) : 125 – 135 .
   Web of Science ®Google Scholar
• Kalyanova , R. , Petrovskii , P. and Mastryukova , T. 2002 . Synthesis and Intramolecular Cyclization of ω-Haloalkyl Dithiophosporus Acid Esters . Phosphorus, Sulfur, and Silicon and the Related Elements , 177 ( 8–9 ) : 2225 – 2226 .
   Web of Science ®Google Scholar
• Lin , I.J.B. , Lai , J.S. and Liu , C.W. 1990 . Phase-Transfer-Catalyzed P-C Bond Cleavage in Platinum bis(Diphenylphosphino)methane Complexes under Exceedingly Mild Conditions . Organometallics , 9 ( 2 ) : 530 – 531 .
   Web of Science ®Google Scholar
• Kim , D.Y. , Suh , K.H. , Huh , S.C. and Lee , K. 2001 . Michael Addition of n-(Diphenylmethylene) Aminomethylphosphonate to Acrylates Using Phase Transfer Catalysis Conditions: Synthesis of 1-(n-Diphenylmethylene)amino-3-(alkoxycarbonyl)-Propylphosphonates . Synthetic Comm. , 31 ( 21 ) : 3315 – 3322 .
   Web of Science ®Google Scholar
• Zhang , H.M. , Guo , Q.Z. and Chen , T.L. 2004 . Synthesis, Characterization and Ring-Opening Polymerization of Cyclic (Arylene Phosphonate) Oligomers . Chin. J. Polymer Sci. , 22 ( 1 ) : 83 – 89 .
   Web of Science ®Google Scholar
• Howell , J.A.S. 1997 . The Phase-Transfer-Catalyzed Preparation of Mo(CO)4(Diphos) . J. Chem. Ed. , 74 ( 5 ) : 577 – 579 .
   Web of Science ®Google Scholar
• Fox , D.L. , Whitely , N.R. , Cohen , R.J. and Salvatore , R.N. 2003 . Phosphonodithioformates: Efficient Three-Component Coupling of Dialkyl Phosphites, Carbon Disulfide, and Alkyl Halides in the Presence of Cesium Carbonate and Tetrabutylammonium Iodide . Synlett , : 2037 – 2041 .
   Web of Science ®Google Scholar
• Ilia , G. , Iliescu , S. , Macarie , L. and Popa , A. 2008 . Synthesis of Tervalent Phosphorus Esters in Biphasic System Using Potassium Phosphate as a Unique Base . Heteroatom Chemistry , 19 ( 4 ) : 360 – 364 .
   Web of Science ®Google Scholar
• Mlotkowska , B. and Zwierzak , A. 1978 . Solid Naoh/K2CO3—A New Highly Effective Base for Phase-Transfer Catalysed N-Alkylation of Diphenylphosphinic Hydrazide . Tetrahedron Lett. , 19 ( 47 ) : 4731 – 4734 .
   Google Scholar
• Augenstein , M. and Wegner , G. 1988 . Synthesis and Reactivity of 1,4-Disubstituted Butadienes in the Solid State . Makromol. Chem. , 189 ( 1 ) : 163 – 184 .
   Web of Science ®Google Scholar
• Zwierzak , A. 1984 . N-Alkylation of Diethyl N-Alkylphosphoramidates in an Anhydrous Medium . Synthesis , 332
   Google Scholar
• D'Incan , E. and Seyden-Penne , J. 1975 . Ion Pair Extraction: Alkylation of Phosphonates and the Wittig/Horner Reaction . Synthesis , 516
   Google Scholar
• Blumenkopf , T.A. 1986 . An Efficient Preparation of Diethyl Phenylsulfonylmethyl Phosphonate . Synthetic Comm. , 16 ( 2 ) : 139 – 147 .
   Web of Science ®Google Scholar
• Aboujaoude , E.E. , Collignon , N. , Savignac , P. and Bensoam , J. 1987 . Synthesis of ω-amino-ω-carboxyl-alkylphosphonic acids . Phosphorus, Sulfur, and Silicon and the Related Elements , 34 ( 3–4 ) : 93 – 104 . (in Frenceh)
   Web of Science ®Google Scholar