α-Hydroxyiminophosphonate, -phosphinate and -phosphonium Derivatives

Current Organic Synthesis

Volumn 7, Issue 6, 2010, Pages 628-649

  Vicario, Javier ^a   Alonso, Concepción ^a   de Los Santos, Jesús M ^a   Palacios, Francisco ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Aminophosphonic acids; Beckmann rearrangement; Iminophosphinates; Iminophosphonates; Iminophosphonium salts

Indexed keywords

EID: 79953740125     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017910794328583     Document Type: Article

References (103)

1. Taneja, H. K.; Roy, N. K. Studies on dialkyl chloroacylphosphonates and their oxime derivatives as fungicides. J. Inst. Chem. (India) 1989, 61, 28-30.
2. Roy, N. K.; Taneja, H. K. Synthesis of aroyl phosphonates and oximes and their antifungal activity. Int. J. Trop. Agric. 1989, 7, 142-146.
3. Roy, N. K.; Taneja, H. K. Evaluation of dialkyl acyl phosphonates and their oximes as potential fungicides. Int. J. Trop. Agric. 1987, 5, 215-222.
4. Golomb, G.; Schlossman, A.; Eitan, Y.; Saadeh, H.; Van Gelder, J. M.; Breuer, E. In vitro and in vivo anticalcification effects of novel bishydroxyiminophosphonates. J. Pharm. Sci. 1992, 81, 1004-1007
5. Breuer, E.; Golomb, G.; Hoffman, A.; Schlossman, A.; Van Gelder, J. M.; Saadeh, H.; Levi, M.; Eitan, Y. In vitro and in vivo inhibition of hydroxyapatite formation and dissolution by bisacylphosphonates and bishydroxyiminophosphonates. Phosphorus Sulfur Silicon Relat. Elem. 1993, 76, 427-430.
6. Breuer, E.; Safadi, M.; Chorev, M.; Gibson, D. Novel amino acid derivatives. preparation and properties of aminoacylphosphonates and amino hydroxyimino phosphonates. J. Org. Chem. 1990, 55, 6147-6153.
7. Breuer, E.; Karaman, R.; Goldblum, A.; Gibson, D.; Leader, H.; Potter, B. V. L.; Cummins, J. H. α-Oxyiminophosphonates: Chemical and physical properties. Reactions, theoretical calculations, and x-ray crystal structures of (E)- and (Z)-dimethyl α- hydroxyiminobenzylphosphonates. J. Chem. Soc., Perkin Trans. 1 1988, 3047-3057.
8. Kim, K. S.; Hurh, E. Y.; Youn, J. N.; Park, J. I. Dialkyl (1- hydroxyiminoalkyl)phosphonates from 1-bromo-1-nitroalkanes and trialkyl phosphites. J. Org. Chem. 1999, 64, 9272-9274.
9. Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I. Easy and efficient synthesis of enantiomerically enriched 2H-azirines derived from phosphonates. Tetrahedron Lett. 2000, 41, 5363-5366
10. Palacios, F.; Aparicio, D.; Ochoa de Retana, A. M.; de los Santos, J. M.; Gil, J. I.; Alonso, J. M. Asymmetric synthesis of 2H-Azirines derived from phosphine oxides using solid-supported amines. Ring opening of azirines with carboxylic acids. J. Org. Chem. 2002, 67, 7283-7288
11. Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I.; López de Munain, R. Synthesis of Pyrazine-phosphonates and - Phosphine Oxides from 2H-Azirines or Oximes. Org. Lett. 2002, 4, 2405-2408
12. Palacios, F.; Aparicio, D.; Ochoa de Retana, A. M.; de los Santos, J. M.; Gil, J. I.; López de Munain, R. Asymmetric synthesis of 2H-aziridine phosphonates, and α- or α- aminophosphonates from enantiomerically enriched 2H-azirines. Tetrahedron Asymmetry 2003, 14, 689-700.
13. Conti, P.; Pinto, A.; Tamborini, L.; Dunkel, P.; Gambaro, V.; Visconti, G. L.; De Micheli, C. A regioselective route to 5-substituted isoxazole- and isoxazoline-3-phosphonates. Synthesis 2009, 591-596.
14. Boyer, S. H.; Jiang, H.; Jacintho, J. D.; Reddy, M. V.; Li, H.; Li, W.; Godwin, J. L.; Schulz, W. G.; Cable, E. E.; Hou, J.; Wu, R.; Fujitaki, J. M.; Hecker, S. J.; Erion, M. D. Synthesis and biological evaluation of a series of liver-selective phosphonic acid thyroid hormone receptor agonists and their prodrugs. J. Med. Chem. 2008, 51, 7075-7093.
15. Anderson, D. W.; Campbell, M. M.; Malik, M.; Prashad, M.; Wightman, R. H. Phosphonopeptides and 3-aminophosphononocardicinic acid. Tetrahedron Lett. 1990, 31, 1759-1762.
16. Ntai, I.; Bachmann, B. O. Identification of ACE pharmacophore in the phosphonopeptide metabolite K-26. Bioorg. Med. Chem. Lett. 2008, 18, 3068-3071.
17. Guimaraes, E.; Lemos, A.; Lopes, M. Reactions of nitrosovinylphosphonates with electron-rich alkenes and heterocycles. Phosphorus Sulfur Silicon Relat. Elem. 2007, 182, 2149-2155.
18. Clement, J.; Frejaville, C.; Tordo, P. DEPMPO and lipophilic analogs: Synthesis and EPR studies. Res. Chem. Intermed. 2002, 28, 175-190.
19. Quiclet-Sire, B.; Zard, S. Z.; Zhang, H. A practical access to α- phosphonoenamides. J. Organomet. Chem. 2002, 643-644, 404-408.
20. Ta-Shma, R.; Schneider, H.; Mahajna, M.; Katzhendler, J.; Breuer, E. A kinetic study of competing fragmentation and hydrolyses of phenyl hydrogen α-hydroxyiminobenzylphosphonate - a case of acid mediated inhibition of acid catalysis. J. Chem. Soc. Perkin Trans. 2 2001, 1404-1407
21. Bligh, S. W. A.; Choi, N.; McGrath, C. M.; McPartlin, M.; Woodroffe, T. M. Synthesis and structural properties of metal complexes of dialkyl α-hydroxyiminophosphonates. J. Chem. Soc. Dalton Trans. 2000, 2587-2594.
22. Zon, J.; Amrhein, N.; Gancarz, R. Inhibitors of phenylalanine ammonialyase: 1-aminobenzylphosphonic acids substituted in the benzene ring. Phytochemistry 2002, 59, 9-21.
23. Depature, M.; Diewok, J.; Grimaldi, J.; Hatem, J. Tin-mediated free-radical cyclization of α-allenylbenzoyloximes. Eur. J. Org. Chem. 2000, 275-280.
24. Breuer, E.; Zaher, H.; Tashma, Z.; Gibson, D. Acylphosphonamidates and α-hydroxyiminophosphonamidates. Synthesis of Nacylphosphorodiamidates by Beckmann rearrangement. Crystal structure of (E)-α-hydroxyiminobenzyl-1-pyrrolidinylphosphinate. Heteroat. Chem. 1996, 7, 515-520.
25. Boivin, J.; Schiano, A. M.; Zard, S. Z. Iminyl radicals by stannane mediated cleavage of oxime esters. Tetrahedron Lett. 1994, 35, 249-252
26. Boivin, J.; Callier-Dublanchet, A.; Quiclet-Sire, B.; Schiano, A.; Zard, S. Z. Iminyl, amidyl, and carbamyl radicals from O-benzoyl oximes and O-benzoyl hydroxamic acid derivatives. Tetrahedron 1995, 51, 6517-6528.
27. Mahajna, M.; Breuer, E. 2-Cyanoethyl and p-nitrophenethyl α- hydroxyimino- and α-methoxyiminophosphonates: Potential precursors of metaphosphate anion. J. Chem. Soc., Perkin Trans. 1 1994, 1847-1849.
28. Breuer, E.; Mahajna, M. Synthesis and reactions of 2,2,2- trihaloethyl α-hydroxyiminobenzylphosphonates. The influence of the ester group on the chemistry of phosphonates. Heteroat. Chem. 1992, 3, 251-260.
29. Rogers, R. S.; Stern, M. K. An improved synthesis of the phosphonic acid analog of tryptophan. Synlett 1992, 708.
30. Subotkowski, W.; Kowalik, J.; Tyka, R.; Mastalerz, P. The phosphonic analog of tryptophan. Pol. J. Chem. 1981, 55, 853-857.
31. Breuer, E.; Mahajna, M.; Quin, L. D.; Quin, G. S. Photoinduced phosphorylation by [α-(hydroxyimino)benzyl]phosphonates through fragmentation to monomeric metaphosphates. J. Org. Chem. 1991, 56, 4791-4793.
32. Maier, L.; Diel, P. J. Organic phosphorus compounds. 97. Synthesis and properties of 1-amino-2-aryl- and 2-pyridylethylphosphonic acids and derivatives. Phosphorus Sulfur Silicon Relat. Elem. 1991, 62, 15-27.
33. Breuer, E.; Schlossman, A.; Safadi, M.; Gibson, D.; Chorev, M.; Leader, H. Stereoselectivity in fragmentation and rearrangement of α-hydroxyiminophosphinates and -phosphonates. A synthetic approach to acylphosphon- and phosphoramidates. Crystal structures of methyl (E)-α-hydroxyiminobenzylphenylphosphinate and methyl benzoylphenylphosphonamidate. J. Chem. Soc. Perkin Trans. 1 1990, 3263-3269.
34. Karaman, R.; Goldblum, A.; Breuer, E.; Leader, H. Acylphosphonic acids and methyl hydrogen acylphosphonates: Physical and chemical properties and theoretical calculations. J. Chem. Soc. Perkin Trans. 1 1989, 765-774.
35. Zon, J. Synthesis of diisopropyl 1-nitroalkanephosphonates from diisopropyl 1-oxoalkanephosphonates. Synthesis 1984, 661-663.
36. Stringer, M. J.; Stock, J. A.; Cobb, L. M. Synthesis of a DOPA analog 1-amino-2-(3,4-dihydroxyphenyl)ethylphosphonic acid and distribution studies in mice bearing the harding-passey melanoma. Chem. Biol. Interact. 1974, 9, 411-421.
37. Berlin, K. D.; Roy, N. K.; Claunch, R. T.; Bude, D. A novel route to α-aminoalkylphosphonic acids and dialkyl α- aminoalkylphosphonate hydrochlorides. J. Am. Chem. Soc. 1968, 90, 4494-4495.
38. Sekine, M.; Kume, A.; Hata, T. Dialkyl acylphosphonates: a new acylating agent of alcohols. Tetrahedron Lett. 1981, 22, 3617-3620.
39. Sekine, M.; Satoh, M.; Yamagata, H.; Hata, T. Acylphosphonates: phosphorus-carbon bond cleavage of dialkyl acylphosphonates by means of amines. Substituent and solvent effects for acylation of amines. J. Org. Chem., 1980, 45, 4162-4167.
40. Glebova, Z. I.; Kist'yan, G. K.; Shvets, A. A. Carbohydrate oximes of 2-deoxy-1-ketophosphonates and -phosphinates. Simple synthesis from aldonic acid acetates. Russ. J. Gen. Chem. 1998, 68, 650-651.
41. Berlin, K. D.; Claunch, R. T.; Gaudy, E. T. α-Aminoarylmethylphosphonic acids and diethyl α-aminoarylmethylphosphonate hydrochlorides. Aluminum-amalgam reduction of oximes of diethyl aroylphosphonates. J. Org. Chem. 1968, 33, 3090-3095.
42. Neidlein, R.; Keller, H.; Boese, R. Mild preparation of [1-[(benzyloxy)imino]alkyl]phosphonic dichlorides: Application to the synthesis of cyclic phosphonic diesters and cyclic monoester amides. Heterocycles 1993, 35, 1185-1203
43. Neidlein, R.; Keller, H. Syntheses of 1-benzyloxyaminoalkylphosphonates. Heterocycles 1993, 36, 1925-1932
44. Elhaddadi, M.; Jacquier, R.; Gastal, F.; Petrus, C.; Petrus, F. A convenient synthesis of alkyl and dialkyl 1-benzyloxyamino alkyl phosphonates and phosphinates. Phosphorus Sulfur Silicon Relat. Elem. 1990, 54, 143-150.
45. Eguchi, C.; Akiba, K.; Inamoto, N. Reaction of alkylidenephosphoranes with nitrosyl chloride and decomposition of α-hydroxyimino-phosphonium chlorides formed. Bull. Chem. Soc. Jpn. 1970, 43, 438-442
46. Akiba, K.; Eguchi, C.; Inamoto, N. Formation of α-hydroxyiminophosphonium chlorides by reaction of phosphine-alkylenes with nitrosyl chloride and their decompositions. Bull. Chem. Soc. Jpn. 1967, 40, 2983.
47. Kaushik, M. P.; Vaidyanathaswamy, R. Synthesis and characterization of oximino pyridoyl phosphonates. Phosphorus Sulfur Silicon Relat. Elem. 1995, 102, 45-50.
48. Shiraki, C.; Saito, H.; Takahashi, K.; Urakawa, C.; Hirata, T. Preparation of amino(diethoxyphosphoryl)acetic esters. Catalytic hydrogenation of diazo compounds to amines. Synthesis 1988, 399-401.
49. Carrick, J. M.; Kashemirov, B. A.; McKenna, C. E. Indirect photoinduced phosphorylation via a photolabile troika acid C-ester: Onitrobenzyl (E)-(hydroxyimino)(dihydroxyphosphinyl)acetate. Tetrahedron 2000, 56, 2391-2396.
50. Kashemirov, B. A.; Fujimoto, M.; McKenna, C. E. (E)- (Hydroxyimino)(hydroxymethoxyphosphinyl)acetic acid: Synthesis and pH-dependent fragmentation. Tetrahedron Lett. 1995, 36, 9437-9440.
51. Whitesell, M. A.; Kyba, E. P. Addition of amine nucleophiles to diphosphorylalkynes. The chemistry of the derived enamines. Tetrahedron Lett. 1983, 24, 1679-1682.
52. Tukanova, S. K.; Khegai, V.; Dzhiembaev, B. Z. Reaction of α- chloro-α-isonitrosoacetone with triethyl phosphite. Russ. J. Gen. Chem. 2000, 70, 1819.
53. Kim, K. S.; Hurh, E. Y.; Park, Y. H.; Park, J. I.; Kim, S. S. Reaction of 1-bromo-1-nitropropane and trimethyl phosphite. Bull. Korean Chem. Soc. 1997, 18, 129-130.
54. Trippett, S.; Walker, B. J.; Hoffmann, H. The reaction of triphenylphosphine with 1-bromo-1-nitro-alkanes. J. Chem. Soc. 1965, 7140-7141.
55. Kukhar, V. P.; Hudson, H. R., Eds. In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity. J. Wiley: Chischester, 2000.
56. Grembecka, J.; Kafarski, P. Leucine Aminopeptidase as a target for inhibitor design. Mini-Rev. Med. Chem. 2001, 1, 133-144.
57. Kafarski, P., Lejczak, B. Aminophosphonic acids of potential medical importance. Curr. Med. Chem. Anti-Cancer Agents 2001, 1, 301-312.
58. Palacios, F.; Alonso, C.; de los Santos, J. M. Synthesis of α- aminophosphonates and -phosphinates. Chem. Rev. 2005, 105, 899-931.
59. Palacios, F.; Ochoa de Retana, A. M.; Alonso, J. M. Reaction of 2H-azirine phosphine oxide and -phosphonates with nucleophiles. Stereoselective synthesis of functionalized aziridines and α- and α-aminophosphorus derivatives. J. Org. Chem. 2005, 70, 8895-8901.
60. Palacios, F.; Alonso, C.; de los Santos, J. M. α -Phosphono- and phosphinopeptides derived from α-amino-phosphonic and phosphinic acids. Curr. Org. Chem. 2004, 8, 1481-1496.
61. Breuer, E.; Karaman, R.; Gibson, D.; Leader, H.; Goldblum, A. α- Hydroxyiminophosphonic acids. New types of phosphorylating agents through monomeric metaphosphate. J. Chem. Soc. Chem. Commun. 1988, 504-506.
62. Kashemirov, B. A.; Ju, J.; Bau, R.; McKenna, C. E.Troika acids: Synthesis, structure, and fragmentation pathways of novel α- (hydroxyimino)phosphonoacetic acids. J. Am. Chem. Soc. 1995, 117, 7285-7286.
63. Salomon, C. J.; Breuer, E. Efficient and selective dealkylation of phosphonate diisopropyl esters using Me3SiBr. Tetrahedron Lett. 1995, 36, 6759-6760.
64. Breuer, E.; Karaman, R.; Leader, H.; Goldblum, A. Phosphorylation of alcohols through the acid-catalyzed fragmentation of α- (oxyimino)phosphonates. J. Chem. Soc. Chem. Commun. 1987, 671-672.
65. Mahajna, M.; Breuer, E. Thermal fragmentation of trihaloethyl and hexafluoro-2-propyl α-hydroxyiminobenzylphosphonates. Solvent effects and the trapping of metaphosphate. J. Org. Chem. 1993, 58, 7822-7826.
66. Glebova, Z. I.; Shvets, A. A. Synthesis of a novel carbohydrate P,N-complexone. Russ. J. Gen. Chem. 2000, 70, 1151-1152.
67. Palacios, F.; Vicario, J.; Aparicio, D. Efficient synthesis of 1- azadienes derived from α-aminoesters. Regioselective preparation of α-dehydroamino acids, vinylglycines, and α-amino acids. J. Org. Chem. 2006, 71, 7690-7696.
68. Palacios, F.; Vicario, J.; Maliszewska, A.; Aparicio, D. Synthesis of α-phosphorylated α,α-unsaturated imines and their selective reduction to vinylogous and saturated α-aminophosphonates. J. Org. Chem. 2007, 72, 2682-2685.
69. Palacios, F.; Ochoa de Retana, A. M.; Alonso, J. M. Regioselective synthesis of fluoroalkylated α-aminophosphorus derivatives and aziridines from phosphorylated oximes and nucleophilic reagents. J. Org. Chem. 2006, 71, 6141-6148.
70. Kowalik, J.; Kupczyk-Subotkowska, L.; M/xnamexastalerz/x/namex, P. Preparation of dialkyl 1-aminoalkane phosphonates by reduction of dialkyl 1-hydroxy imino alkane phosphonates with zinc in formic acid. 1- Amino-2-mercaptoethylphosphonic acid, the phosphonic analog of cysteine. Synthesis 1981, 57-58
71. Kowalik, J.; Zygmunt, J.; Mastalerz, P. Pol. J. Chem. 1981, 55, 713-715
72. Oleksyszyn, J.; Gruszecka, E.; Kafarski, P.; Mastalerz, P. New phosphonic analogs of aspartic and glutamic acid by aminoalkylation of trivalent phosphorus chlorides with ethyl acetyloacetate or ethyl levulinate and benzyl carbamate. Monatsh. Chem. 1982, 113, 59-71
73. Lejczak, B.; Kafarski, P.; Makowiecka, E. Phosphonic analogs of tyrosine and 3,4-dihydroxyphenylalanine (dopa) influence mushroom tyrosinase activity. Biochem. J. 1987, 242, 81-88
74. Witkowska, H. E.; Wasielewski, C. Synthesis of derivatives of phosphonic glutathione analogs. Int. J. Pept. Protein Res. 1989, 33, 154-161.
75. Drag, M.; Grembecka, J.; Pawelczak, M.; Kafarski, P. α-Aminoalkylphosphonates as a tool in experimental optimisation of P1 side chain shape of potential inhibitors in S1 pocket of leucine- and neutral aminopeptidases. Eur. J. Med. Chem. 2005, 40, 764-771
76. Ntai, I.; Phelan, V. V.; Bachmann, B. O. Phosphonopeptide K-26 biosynthetic intermediates in astrosporangium hypotensionis. Chem. Commun. 2006, 4518-4520
77. Asano, S.; Kitahara, T.; Ogawa, T.; Matsui, M. Synthesis of α- amino phosphonic acids. Agr. Biol. Chem. 1973, 37, 1193-1195.
78. Bartlett, P. A.; Hunt, J. T.; Adams, J. L.; Gehret, J. C. E. Phosphorus-containing purines and pyrimidines: A new class of transition state analogs. Bioorg. Chem. 1978, 7, 421-436.
79. Green, D.; Patel, G.; Elgendy, S.; Baban, J. A.; Claeson, G.; Kakkar, V. V.; Deadman, J. The facile synthesis of O,O-dialkyl 1- aminoalkanephosphonates. Tetrahedron Lett. 1993, 34, 6917-6920.
80. Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S.; Evin, O. O. A simple synthesis of 1-aminophosphonic acids from 1- hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds. Tetrahedron Lett. 1996, 37, 407-410.
81. Subotkowski, W.; Tyka, R.; Mastalerz, P. Large scale preparation of dialkyl 2-pyrrolidinephosphonates. Pol. J. Chem. 1983, 57, 1389-1391.
82. Yuan, C.; Chen, S.; Zhou, H.; Maier, L. Studies on organophosphorus compounds. LXXV. Facile synthesis of 1- (hydroxyamino)alkyl(or aryl)phosphonic acids. Synthesis 1993, 955-957.
83. Wilt, J. C.; Pink, M.; Johnston, J. N. A diastereo- and enantioselective synthesis of α-substituted anti-α,α-diaminophosphonic acid derivatives. Chem. Commun. 2008, 4177-4179.
84. Al-Dulayymi, J. R.; Baird, M. S.; Pavlov, V.; Kurdjukov, A. I. Phosphorylnitrile oxides. IX. Dipolar cycloaddition of a phosphorylnitrile oxide to functionalized cyclopropenes. Tetrahedron 1996, 52, 8877-8888.
85. de los Santos, J. M.; Ignacio, R.; Aparicio, D.; Palacios, F. Michael addition of amine derivatives to conjugate phosphinyl and phosphonyl nitrosoalkenes. Preparation of α-amino phosphine oxide and phosphonate derivatives. J. Org. Chem. 2007, 72, 5202-5206.
86. de los Santos, J. M.; Ignacio, R.; Aparicio, D.; Palacios, F.; Ezpeleta, J. M. Reactions of Conjugate Phosphinyl- and Phosphonyl- Nitroso Alkenes with Enamines. Preparation of N-Hydroxypyrrole Derivatives. J. Org. Chem. 2009, 74, 3444-3448.
87. Breuer, E. Fragmentations and rearrangements of α-hydroxyiminoalkylphosphonates. Curr. Org. Chem. 2006, 10, 2357-2370.
88. Breuer, E.; Zaher, H.; Tashma, Z. Beckmann rearrangement of N- (α-hydroxyiminoalkylphosphonyl)amino acids. A convenient synthetic approach to novel peptide transition state analogs. Tetrahedron Lett. 1992, 33, 2067-2068.
89. Kaushik, M. P.; Vaidyanathaswamy, R. Beckmann rearrangement of aroylphosphonate oximes: A reinvestigation. Chem. Ind. 1989, 389.
90. Schlossman, A.; Gibson, D.; Breuer, E. Rearrangement and fragmentation reactions of α-hydroxyiminophosphinates. On the nature of the metaphosphonate intermediate involved in phosphonylations by α-hydroxyiminophosphinate. Phosphorus Sulfur Silicon Relat. Elem. 1990, 49-50, 81-84.
91. Quin, L. D.; Wu, X. P.; Breuer, E.; Mahajna, M. The mechanism of fragmentation of alkyl α-(oxyimino)benzylphosphonates; use of silica gel as a novel hydroxylic trapping reactant for an intermediate alkyl metaphosphate. Tetrahedron Lett. 1990, 31, 6281-6282.
92. Katzhendler, J.; Schneider, H.; Ta-Shma, R.; Breuer, E. J. Fragmentation of methyl hydrogen α-hydroxyiminobenzylphosphonates - Kinetics, mechanism and the question of metaphosphate formation. J. Chem. Soc., Perkin Trans. 2 2000, 1961-1968.
93. Kehler, J.; Breuer, E. Unusual solvent-dependent behavior of hydroxyiminophosphonamidates in the Beckman reactions: Choice between rearrangement or fragmentation to metaphosphonamidate species. Chem. Commun. 1997, 1751-1752.
94. [77] Il'yasov, A. V.; Vafina, A. A.; Breuer, E.; Haegele, G. EPR study of some iminoxy free radicals generated from phosphorylated oximes and dioximes. Appl. Magn. Reson. 1998, 14, 489-496
95. Chmielewski, P. J.; Jezierski, A.; Siatecki, Z.; Sienkiewicz, J. An ESR study on formation of iminoxy free radicals - solvent effect on hyperfine splitting constants. Radiat. Phys. Chem. 1995, 45, 891-897
96. Chmielewski, P. J.; Jezierski, A.; Siatecki, Z. Iminoxy free radicals derived from diethyl (1-hydroxyimino)phosphonates. An EPR study. J. Chem. Soc. Perkin Trans. 2 1992, 1421-1424
97. Siatecki, Z.; Chmielewski, P. J.; Jezierski, A. Phosphorus-31 hyperfine interaction in a new type of phosphorus-containing iminoxy free radicals. An ESR study. Magn. Reson. Chem. 1992, 30, 163-168.
98. Boivin, J.; Schiano, A.; Zard, S. Z.; Zhang, H. A new method for the generation and capture of iminyl radicals. Tetrahedron Lett. 1999, 40, 4531-4534.
99. Bligh, S. W. A.; Choi, N.; Green, D. S. C.; Hudson, H. R.; McGrath, C. M.; McPartlin, M.; Pianka, M. Transition metal complexes of dialkyl α-hydroxyiminophosphonates, a novel class of metal complexes. Polyhedron 1993, 12, 2887-2890.
100. Lisowski, J.; Starynowicz, P.; Jezierski, A.; Siatecki, Z. Tetrameric Nickel(II) complex with diethyl 1-hydroxyiminobenzylphosphonate. Polyhedron 1996, 15, 3589-3593.
101. Bligh, S. W. A.; Choi, N.; Hudson, H. R.; McGrath, C. M.; McPartlin, M. Synthesis of the first lanthanide complexes of dialkyl α- hydroxyiminophosphonates; ambivalent ligand bonding in the PrIII complexes of diisopropyl α-hydroxyiminopropylphosphonate (L1), [PrL1 3Cl3] and [NdL1 2(NO3)3(H2O)]. J. Chem. Soc. Dalton Trans. 1994, 2335-2337.
102. Gibson, D.; Karaman, R. α-Hydroxyimino phosphonic acid derivatives. Separation of E and Z isomers by metal chelation and the preparation and characterization of copper bis [(E)-(α- (hydroxyimino)benzyl)phosphonate]-water. Inorg. Chem. 1989, 28, 1928-1932.
103. Gibson, D.; Karaman, R. Metal complexes of α- hydroxyiminophosphonic acid derivatives. Preparation and crystal structures of calcium and cadmium complexes of methyl (E)-α- hydroxyiminobenzylphosphonate. J. Chem. Soc. Dalton Trans. 1989, 1911-1914.