Polyfluoroaromatic compounds with a -N=CClR group - A reactive type of polyfluoroarene

Journal of Fluorine Chemistry

Volumn 126, Issue 6, 2005, Pages 860-876

  Petrova, Tamara D ^a   Platonov, Vyacheslav E ^a  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

AlCl 3; Carbonimidoyl dichlorides; Imidoylchlorides; Polyfluoroarenes

Indexed keywords

EID: 20744436107     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2005.04.003     Document Type: Review

References (84)

1. H. Ulrich The Chemistry of Imidoyl Halides 1968 Plenum Press New York
2. R. Bonnet S. Patai The Chemistry of the Carbon Nitrogen Double Bond 1970 Wiley/Interscience London 597 662
3. E. Kühle, B. Anders, E. Klauke, H. Tarnow, and G. Zumach Angew. Chem. Int. Ed. 8 1969 20 34
4. T.D. Petrova, and V.E. Platonov Uspechi Khim. 56 1987 1973 2000 [Chem. Abstr. 108 (1988) 93800x].
5. T.D. Petrova, and V.E. Platonov Uspechi Khim. 57 1988 405 433 [Chem. Abstr. 108 (1988) 166669y].
6. W. Kantlehner, and W.W. Mergen A.R. Katritzky O. Meth-Cohn C.W. Rees Comprehensive Organic Functional Group Transformation vol. 5 1995 Pergamon Press New York 654 723
7. S. Fustero, A. Navaro, D. Diaz, M.G. de la Torre, A. Asensio, F. Sanz, and M.L. Gonzales J. Org. Chem. 61 1996 8849 8859
8. K. Uneyama J. Fluorine Chem. 97 1999 11 25
9. A.Ya. Aizikovich, V.N. Charushin, and O.N. Chupakhin Khim. Farm. Zh. 30 1996 43 45 [Chem.Abstr. 125 (1996) 328482n].
10. T. Takematsu, T. Komata, T. Kume, J. Kohda, K. Susuki, M. Kawamura, Y. Ikeda, K. Mori, WO Patent 9,519,962 (1995)
11. [Chem. Abstr. 123 (1995) P 339403x].
12. S.E. Lopez, O. Rebollo, J. Salazar, J.E. Charris, and C. Yanez J. Fluorine Chem. 120 2003 71 75
13. Ya. Shen, and T. Wang J. Fluorine Chem. 82 1997 139 141 (and references therein)
14. B. Al-Saleh, R.E. Banks, M.G. Barlow, and J.C. Hornby J. Fluorine Chem. 12 1978 341 344
15. T.I. Savchenko, T.D. Petrova, V.E. Platonov, and G.G. Yakobson J. Fluorine Chem. 9 1977 505 508
16. T.I. Savchenko, T.D. Petrova, V.E. Platonov, and G.G. Yakobson Zh. Org. Khim. 15 1979 1018 1024 [Chem. Abstr. 91 (1979) 91269n].
17. T.I. Savchenko, T.D. Petrova, V.E. Platonov, and G.G. Yakobson Zh. Org. Khim. 15 1979 1025 1029 [Chem. Abstr. 91 (1979) 91270f].
18. T.I. Savchenko, T.D. Petrova, I.V. Kolesnikova, and V.E. Platonov Izv. Akad. Nauk SSSR, Ser. Khim. 1980 1213 [Chem. Abstr. 93 (1980) 132182r].
19. T.I. Savchenko, I.V. Kolesnikova, T.D. Petrova, and V.E. Platonov J. Fluorine Chem. 22 1983 439 458
20. T.D. Petrova, A.G. Ryabichev, T.I. Savchenko, V.E. Platonov, V.I. Mamatyuk, Yu.V. Gatilov, and I.Yu. Bagryanskaya Zh. Org. Khim. 22 1986 1297 1306 [J. Org. Chem. USSR, 22 (1986) 1168-1176 (Engl. Transl.)].
21. T.D. Petrova, V.E. Platonov, unpublished data.
22. L.S. Sologub, A.A. Kisilenko, V.P. Kuchar', and S.I. Vdovenko Khim. Getrocycl. Soedin. 1983 798 800 [Chem. Abstr. 99 (1983) 122246z].
23. D. Lentz, K. Graske, and D. Preugschat Chem. Ber. 121 1988 1445 1447
24. I.V. Kolesnikova, A.G. Ryabichev, T.D. Petrova, and V.E. Platonov Izv. Akad. Nauk SSSR, Ser. Khim. 1988 1651 1654 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 37 (1988) 1466-1469 (Engl. Transl.)].
25. V.A. Petrov J. Fluorine Chem. 109 2001 123 128
26. T.D. Petrova, I.S. Popova, I.V. Kolesnikova, and V.E. Platonov Izv. Akad. Nauk, Ser. Khim. 1994 1089 1094 [Russ. Chem. Bull. 43 (1994) 1027-1033 (Engl. Transl.)]
27. V.I. Markov, I.I. Groshevoy, V.P. Pedan, L.S. Karpishchenko, and L.G. Sinel'nikova Ukr. Khim. Zh. 48 1982 663 664 [Chem. Abstr. 97 (1982) 127209h].
28. Yu.P. Kitaev, B.I. Buzikin, Hydrazones, Nauka, Moscow, 1974, pp. 151-189 (in Russian).
29. B.I. Buzikin, and G.D. Lezhnina Yu.P. Kitaev The Chemistry of Hydrazones 1977 Nauka Moscow 120 152 (in Russian)
30. K.V. Dvornikova, V.E. Platonov, and G.G. Yakobson Zh. Org. Khim. 27 1991 609 618 [J. Org. Chem. USSR, 27 (1991) 525-532 (Engl. Transl.)].
31. T.D. Petrova, Dissertation Thesis (D.Sc.). Novosibirsk, Russia, 1995.
32. G.A. Olah, G. Rasul, A.K. Yudin, A. Burrichter, G.K.S. Prakash, A.L. Chistyakov, I.V. Stankevich, I.S. Akhrem, N.P. Gambaryan, and M.E. Vol'pin J. Am. Chem. Soc. 118 1996 1446 1451
33. G.A. Olah, G. Rasul, L. Heiliger, and G.K.S. Prakash J. Am. Chem. Soc. 118 1996 3580 3583
34. G. Frenking, S. Fau, Ch.M. Marchand, and H. Grützmacher J. Am. Chem. Soc. 119 1997 6648 6655
35. N.R. Ayyangar, R.J. Lahoti, K.V. Srinivasan, and T. Daniel Synthesis 1991 322 324
36. G. Birke, H.P. Latscha, and A. Smidt Z. Anorg. Allg. Chem. 424 1976 287 295
37. M.S. Newman, and A.G. Pinkus J. Org. Chem. 19 1954 978 984
38. O. Paleta Fluor. Chem. Rev. 8 1978 39 68
39. D.P.N. Satchell, and R.S. Satchell Chem. Rev. 69 1969 251 278
40. R. Koppang J. Fluorine Chem. 16 1980 479 482
41. T.D. Petrova, V.E. Platonov, T.I. Savchenko, and L.M. Meshalkina Izv. Akad. Nayk SSSR, Ser. Khim. 1978 2635 2637 [Chem. Abstr. 90 (1979) 71849c].
42. G.M. Brooke, R.D. Chambers, W.K.R. Musgrave, R.A. Storey, and J. Yeadon J. Chem. Soc., Perkin Trans. I 1976 162 166
43. E.N. Kryutchkova, I.V. Kolesnikova, L.P. Drizhd, V.A. Savelova, T.D. Petrova, and V.E. Platonov Zh. Org. Khim. 24 1988 2042 2046 [J. Org. Chem. USSR, 24 (1988) 1840-1844 (Engl. Transl.)]
44. O.M. Polumbrik, I.G. Ryabokon', and L.N. Markovskii Khim. Getrocycl. Soedin. 1980 1130 1133 [Chem. Abstr. 94 (1981) 30716w].
45. T.D. Petrova, T.I. Savchenko, V.E. Platonov, and G.G. Yakobson Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk 1981 109 116 [Chem. Abstr. 96 (1982) 68514h].
46. A.J. Speciale, and L.R. Smith J. Am. Chem. Soc. 84 1962 1868 1876
47. K. Tamura, H. Muzukami, K. Maeda, H. Watanabe, and K. Uneyama J. Org. Chem. 58 1993 32 35
48. I.V. Kolesnikova, T.D. Petrova, V.E. Platonov, T.G. Ryabicheva, V.A. Mikhailov, A.A. Popov, and V.A. Savelova Zh. Org. Khim. 25 1989 1689 1695 [J. Org. Chem. USSR, 25 (1989) 1523-1529 (Engl. Transl.)]
49. I.V. Kolesnikova, T.D. Petrova, V.E. Platonov, V.A. Mikhailov, A.A. Popov, and V.A. Savelova J. Fluorine Chem. 40 1988 217 246
50. K. Uneyama, and M. Kobayashi Tetrahedron Lett. 32 1991 5981 5986
51. K.C. Joshi, R. Jain, A. Dandia, and K. Sharma J. Fluorine Chem. 56 1992 1 27
52. Yu.V. Tonevitsky, D.M. Mognonov, D.B. Sanzhizhapov, Zh.P. Mazurevskajya, and A.V. Toktonov Izv. Akad. Nauk, Ser. Khim. 1999 626 627 [Russ. Chem. Bull. 48 (1999) 620 (Engl. Transl.)]
53. V.A. Mikhailov, I.V. Kolesnikova, A.A. Popov, T.D. Petrova, V.E. Platonov, and V.A. Savelova Zh. Org. Khim. 25 1989 1030 1035 [J. Org. Chem. USSR, 25 (1989) 927-932 (Engl. Transl.)]
54. S.M. Benomar, N.J. O'Reilly, and A.E. Tipping J. Fluorine Chem. 51 1991 207 216
55. V.A. Mikhailov, V.A. Savelova, A.A. Popov, T.D. Petrova, and V.E. Platonov Zh. Org. Khim. 39 2003 1187 1195 [Russ. J. Org. Chem., 39 (2003) 1116-1124 (Engl. Transl.)]
56. E. Kühle Angew. Chem. 74 1962 861 866
57. V.A. Savelova, and A.F. Popov Zh. Org. Chem. 35 1999 821 852 [Russ. J. Org. Chem., 35 (1999) 797-828 (Engl. Transl.)]
58. J.E. Johnson, S.L. Todd, S.M. Dutson, A. Chafouripour, R.M. Alderman, and M.R. Hotema J. Org. Chem. 57 1992 4648 4653
59. A.F. Hegarty, and K.J. Digman J. Chem. Soc., Perkin Trans. II 1975 1046 1051
60. R. Bacaloglu, and T. Korodi Rev. Roum. Chim. 24 1979 1165 1175 [Chem. Abstr. 92 (1980) 110201y].
61. V.A. Savelova, A.A. Popov, T.D. Petrova, V.E. Platonov, and V.A. Mikhailov Theor. Exp. Khim. 39 2003 22 26 [Chem. Abstr. 139 (2003) 213954q]
62. V.A. Mikhailov, A.A. Popov, V.A. Savelova, I.V. Kolesnikova, T.D. Petrova, and V.E. Platonov Zh. Org. Khim. 25 1989 1683 1688 [J. Org. Chem. USSR, 25 (1989) 1517-1522 (Engl. Transl.)]
63. V.A. Mikhailov, D.S. Yufit, E.Yu. Balabanov, Yu.T. Struchkov, A.A. Popov, V.A. Savelova, I.V. Kolesnikova, T.D. Petrova, and V.E. Platonov J. Phys. Org. Chem. 6 1993 319 325
64. T.D. Petrova, I.V. Kolesnikova, T.I. Savchenko, and V.E. Platonov Zh. Org. Khim. 20 1984 1197 1204 [J. Org. Chem. USSR, 20 (1984) 1088-1094 (Engl. Transl.)]
65. T.D. Petrova, V.E. Platonov, L.N. Shchegoleva, A.M. Maksimov, A. Haas, M. Schelvis, and M. Lieb J. Fluorine Chem. 79 1996 13 25
66. L.M. Yagupolskii, Aromatic and Heterocyclic Compounds with Fluoro-containing Substituents, Naukova Dumka, Kiev, 1988, pp. 275, 280 (in Russian).
67. W.A. Sheppard J. Am. Chem. Soc. 87 1965 4338 4341
68. T.I. Savchenko, T.D. Petrova, I.V. Kolesnikova, and V.E. Platonov J. Fluorine Chem. 16 1980 511 512
69. T.I. Savchenko, I.V. Kolesnikova, T.D. Petrova, V.E. Platonov, in: Proceedings of the Fourth USSR Conference on the Chemistry of Fluoroorganic Compounds, Tashkent, 1982. Paper 63.
70. T.D. Petrova, I.V. Kolesnikova, V.I. Mamatyuk, V.P. Vetchinov, V.E. Platonov, I.Yu. Bagryanskaya, and Yu.V. Gatilov Izv. Akad. Nauk, Ser. Khim. 1993 1605 1611 [Russ. Chem. Bull., 42 (1993) 1540-1546 (Engl. Transl.)]
71. G.M. Dyson, and T. Harrington J. Chem. Soc. 1942 150 153
72. T.D. Petrova, V.E. Platonov, L.M. Pokrovskii, T.V. Rybalova, and Yu.V. Gatilov Collect. Czech. Chem. Commun. 67 2002 1449 1466
73. T.D. Petrova, and V.E. Platonov Zh. Org. Khim. 33 1997 745 749 [Russ. J. Org. Chem., 33 (1997) 684-688 (Engl. Transl.)]
74. R. Bonnet S. Patai The Chemistry of the Carbon Nitrogen Double Bond 1970 Wiley/Interscience London 640
75. T.D. Petrova, V.E. Platonov, I.V. Kolesnikova, T.V. Ribalova, I.Yu. Bagryanskaya, and Yu.V. Gatilov J. Fluorine Chem. 103 2000 63 73
76. J.C. Jochims, R. Abu-El-Halawa, L. Zsolnai, and G. Huttner Chem. Ber. 117 1984 1161 1177
77. S. Conde, C. Corral, and R. Madronero Synthesis 1974 28 29
78. H.J. Shine, and A.K.M. Mansurul Hoque J. Org. Chem. 53 1988 4349 4353
79. H. Meerwein, P. Laasch, R. Mersch, and J. Nentwig Chem. Ber. 89 1956 224 238
80. L.M. Yagupolskii, Aromatic and Heterocyclic Compounds with Fluoro-containing Substituents, Naukova Dumka, Kiev, 1988, pp. 230, 255 (in Russian).
81. T.D. Petrova, and V.E. Platonov Zh. Org. Chem. 41 2005 228 236 [Russ. J. Org. Chem., 41 (2005) (Engl. Transl.)]
82. T.D. Petrova, A.G. Ryabitchev, T.I. Savchenko, I.V. Kolesnikova, and V.E. Platonov Zh. Org. Khim. 24 1988 1513 1517 [J. Org. Chem. USSR, 24 (1988) 1362-1366 (Engl. Transl.)]
83. T.D. Petrova, V.E. Platonov, and L.M. Pokrovskii Izv. Akad. Nauk, Ser. Khim. 2002 504 506 [Russ. Chem. Bull., 51 (2002) 544-546 (Engl. Transl.)]
84. T.D. Petrova, V.E. Platonov, and A.M. Maksimov J. Fluorine Chem. 98 1999 17 28