Aromatic polyazides and high-spin nitrenes

Russian Chemical Bulletin

Volumn 60, Issue 7, 2011, Pages 1274-1285

  Chapyshev, S V ^a  

^a INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

Azides; Energetic materials; High spin states; Molecular magnetism; Nanomaterials; Nitrenes

Indexed keywords

EID: 84862092122     PISSN: 10665285     EISSN: 15739171     Source Type: Journal    
DOI: 10.1007/s11172-011-0195-7     Document Type: Review

References (125)

1. Organic Azides: Synthesis and Applications, Eds S. Brase, K. Banert, Wiley, Chichester, 2010.
2. Azides and Nitrenes, Reactivity, and Utility, Ed. E. F. V. Scriven, Academic Press, New York, 1984.
3. S. Brase, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem., Int. Ed., 2005, 44, 5188.
4. E. F. V. Scriven, K. Turnbull, Chem. Rev., 1988, 88, 297.
5. S. V. Chapyshev, Synlett, 2009, 1.
6. C. Ye, H. Gao, J. A. Boatz, G. W. Drake, B. Twamley, J. M. Shreeve, Angew. Chem., Int. Ed., 2006, 45, 7262.
7. M. H. V. Huynh, M. A. Hiskey, J. G. Archuleta, E. L. Roemer, Angew. Chem., Int. Ed., 2005, 44, 737.
8. M. H. V. Huynh, M. A. Hiskey, J. G. Archuleta, E. L. Roemer, R. D. Gillard, Angew. Chem., Int. Ed., 2004, 43, 5658.
9. E. G. Gillan, Chem. Mater., 2000, 12, 3906.
10. E. Kroke, M. Schwarz, Adv. Mater., 1999, 11, 158.
11. T. Sato, A. Narazaki, Y. Kawaguchi, H. Niino, G. Bucher, Angew. Chem., Int. Ed., 2003, 42, 5206.
12. T. Sato, A. Narazaki, Y. Kawaguchi, H. Niino, G. Bucher, D. Grote, J. J. Wolff, H. H. Wenk, W. Sander, J. Am. Chem. Soc., 2004, 126, 7846.
13. H. Finger, J. Prakt. Chem., 1907, 75, 103.
14. R. M. Moriarty, M. Rahman, G. J. King, J. Am. Chem. Soc., 1966, 88, 842.
15. A. V. Pochinok, V. A. Smirnov, S. B. Brichkin, V. Ya. Pochinok, L. F. Avramenko, T. F. Grigorenko, Khim. Vysokikh Energii, 1982, 16, 151
16. High Energy Chem. (Engl. Transl.), 1982, 16.
17. T. Nakai, K. Sato, D. Shiomi, T. Takui, K. Itoh, M. Kozaki, K. Okada, Mol. Cryst. Liq. Cryst., 1999, 334, 157.
18. V. Ya. Pochinok, L. F. Avramenko, T. F. Grigorenko, A. V. Pochinok, I. A. Sidorenko, L. N. Bovchalyuk, Ukr. Khim. Zh. (Ukr. Chem. J.) 1979, 45, 975 (in Russian).
19. A. V. Pochinok, N. I. Sharykina, T. A. Bukhtiyarova, Fiziolog. Aktiv. Veshchestva (Physiologically Active Substances), 1990, 22, 76 (in Russian).
20. S. V. Chapyshev, V Vseross. nauchn. konf. "Energeticheskie kondensirovannye sistemy" (The V All-Russian Scientific Conf. "Energetic Condensed Systems") (Chernogolovka, October 26 - 28, 2010), Abstr., Moscow, 2010, p. 68 (in Russian).
21. D. Adam, K.Karaghiosoff, T. M. Klapotke, G. Holl, V. Kaiser, Propellants, Explosives, Pyrotechnics, 2002, 27, 7.
22. D. S. Breslow, A. F. Marcantonio, US Pat. 3297674; Chem. Abstrs, 1967, 66, 56182.
23. V. N. Boiko, I. V. Gogoman, G. M. Shchupak, L. M. Yagupol'skii, Zh. Org. Khim., 1987, 23, 2586
24. J. Org. Chem. USSR (Engl. Transl.), 1987, 23.
25. T. Wasserman, R. Schueller, W. A. Yager, Chem. Phys. Lett., 1968, 2, 259.
26. S. V. Chapyshev, E. Ya. Misochko, A. V. Akimov, V. G. Dorokhov, P. Neuhaus, D. Grote, W. Sander, J. Org. Chem., 2009, 74, 7238.
27. S. Marburg, P. A. Crieco, Tetrahedron Lett., 1966, 1305.
28. J. G. Morse, L. P. Kuhn, US Clearinghouse Fed. Sci. Tech. Inform. AD, 1970, No. 713665, 20 p.;
29. Chem. Abstrs, 1971, 75, 19826.
30. Yu. M. Mikhailov, S. V. Chapyshev, V. V. Nedel'ko, Izv. Akad. Nauk, Ser. Khim., 2009, 2034
31. Russ. Chem. Bull., Int. Ed., 2009, 58, 2097.
32. S. D. Moshchitskii, F. F. Zeikan', A. F. Pavlenko, V. P. Kukhar', Khim. Geterotsikl. Soedin., 1979, 1492
33. Chem. Heterocycl. Compd. (Engl. Transl.), 1979, 15, 1197.
34. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 1993, 1650
35. Chem. Heterocycl. Compd. (Engl. Transl.), 1993, 29, 1426.
36. S. V. Chapyshev, T. Ibata, Heterocycles, 1993, 36, 2185.
37. S. V. Chapyshev, U. Bergstrasser, M. Regitz, Khim. Geterotsikl. Soedin., 1996, 67
38. Chem. Heterocycl. Compd. (Engl. Transl.), 1996, 32, 59.
39. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 2001, 1056
40. Chem. Heterocycl. Compd. (Engl. Transl.), 2001, 37, 968.
41. S. V. Chapyshev, Mendeleev Commun., 1999, 9, 164.
42. S. V. Chapyshev, N. V. Chapysheva, D. V. Korchagin, G. V. Shilov, Yu. M. Mikhailov, III Vseross. nauchn. konf. "Energeticheskie kondensirovannye sistemy" (The III All-Russian Scientific Conf. "Energetic Condensed Systems") (Chernogolovka, October 31 - November 2, 2006), Abstr., Moscow, 2006, p. 208 (in Russian).
43. S. V. Chapyshev, U. Bergstrasser, M. Regitz, Izv. Akad. Nauk, Ser. Khim., 1996, 252
44. Russ. Chem. Bull. (Engl. Transl.), 1996, 45, 242.
45. S. V. Chapyshev, V. M. Anisimov, Khim. Geterotsikl. Soedin., 1997, 676
46. Chem. Heterocycl. Compd. (Engl. Transl.), 1997, 33, 587.
47. S. V. Chapyshev, V. M. Anisimov, Khim. Geterotsikl. Soedin., 1997, 1521
48. Chem. Heterocycl. Compd. (Engl. Transl.), 1997, 33, 1315.
49. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 1999, 702
50. Chem. Heterocycl. Compd. (Engl. Transl.), 1999, 35, 632.
51. S. V. Chapyshev, Mendeleev Commun., 1999, 166.
52. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 2000, 1497
53. Chem. Heterocycl. Compd. (Engl. Transl.), 2000, 36, 1289.
54. S. V. Chapyshev, R. Walton, P. M. Lahti, Mendeleev Commun., 2000, 7.
55. S. V. Chapyshev, R. Walton, P. M. Lahti, Mendeleev Commun., 2000, 187.
56. S. V. Chapyshev, M. S. Platz, Mendeleev Commun., 2001, 56.
57. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 2001, 935
58. Chem. Heterocycl. Compd. (Engl. Transl.), 2001, 37, 861.
59. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 2003, 87
60. Chem. Heterocycl. Compd. (Engl. Transl.), 2003, 39, 83.
61. S. V. Chapyshev, Mendeleev Commun., 2007, 287.
62. S. V. Chapyshev, S. I. Kuzina, A. I. Mikhailov, Mendeleev Commun., 2007, 207.
63. S. I. Kuzina, A. I. Mikhailov, S. V. Chapyshev, Dokl. Akad. Nauk, 2007, 418, 341
64. Dokl. Phys. Chem. (Engl. Transl.), 2007, 412, 34.
65. S. I. Kuzina, A. I. Mikhailov, S. V. Chapyshev, Khim. Vysokikh Energii, 2007, 41, 245
66. High Energy Chem. (Engl. Transl.), 2007, 41, 245.
67. S. I. Kuzina, D. V. Korchagin, G. V. Shilov, S. V. Chapyshev, A. I. Mikhailov, S. M. Aldoshin, Dokl. Akad. Nauk, 2008, 418, 341
68. Dokl. Phys. Chem. (Engl. Transl.), 2008, 418, 7.
69. S. I. Kuzina, A. I. Mikhailov, S. V. Chapyshev, D. V. Korchagin, G. V. Shilov, S. M. Aldoshin, Zh. Fiz. Khim., 2008, 82, 2081
70. Russ. J. Phys. Chem. A (Engl. Transl.), 2008, 82, 1870.
71. S. M. Aldoshin, D. V. Korchagin, K. V. Bozhenko, G. V. Shilov, S. V. Chapyshev, Izv. Akad. Nauk, Ser. Fiz., 2008, 72, 1254
72. Bull. Russ. Acad. Sci. Physics (Engl. Transl.), 2008, 72, 1556.
73. D. V. Korchagin, K. V. Bozhenko, S. V. Chapyshev, S. M. Aldoshin, Khim. Vysokikh Energii, 2009, 43, 341
74. High Energy Chem. (Engl. Transl.), 2009, 43, 289.
75. Q. Li, Q.-H. Fan, L.-H. Zhang, X.-S. Ye, Synlett, 2006, 2464.
76. L. C. Campeau, P. D. O'Shea, Synlett, 2011, 57.
77. P. T. Nyffeler, C.-H. Liang, K. M. Koeller, J. Am. Chem. Soc., 2002, 124, 10773.
78. P. R. Sridhar, K. R. Prabhu, S. Chandrasekaran, J. Org. Chem., 2003, 68, 5261.
79. W. Weltner, Jr., Magnetic Atoms and Molecules, Dover Publications, New York, 1989.
80. A. Rajca, Chem. Rev., 1994, 94, 871.
81. Magnetic Properties of Organic Materials, Ed. P. M. Lahti, Marcel Dekker, New York, 1999.
82. S. Murata, H. Iwamura, J. Am. Chem. Soc., 1991, 113, 5547.
83. T. A. Fukuzawa, K. Sato, A. S. Ichimura, T. Kinoshita, T. Takui, K. Itoh, P. M. Lahti, Mol. Cryst. Liq. Cryst., 1996, 278, 253.
84. R. S. Kalgutkar, P. M. Lahti, J. Am. Chem. Soc., 1997, 119, 8784.
85. Y. Miura, H. Oka, Y. Teki, Bull. Chem. Soc. Jpn, 2001, 74, 385.
86. N. Oda, T. Nakai, K. Sato, D. Shiomi, M. Kozaki, K. Okada, T. Takui, Mol. Cryst. Liq. Cryst., 2002, 376, 501.
87. R. S. Kalgutkar, P. M. Lahti, Tetrahedron Lett., 2003, 44, 2625.
88. R. A. Evans, M. W. Wong, C. Wentrup, J. Am. Chem. Soc., 1996, 118, 4009.
89. S. V. Chapyshev, A. Kuhn, M. W. Wong, C. Wentrup, J. Am. Chem. Soc., 2000, 122, 1572.
90. S. V. Chapyshev, C. Wentrup, Khim. Geterotsikl. Soedin., 2001, 1219
91. Chem. Heterocycl. Compd. (Engl. Transl.), 2001, 37, 1119.
92. S. V. Chapyshev, Mendeleev Commun., 2002, 227.
93. S. V. Chapyshev, Mendeleev Commun., 2003, 53.
94. S. V. Chapyshev, H. Tomioka, Bull. Chem. Soc. Jpn, 2003, 76, 2075.
95. S. V. Chapyshev, Izv. Akad. Nauk, Ser. Khim., 2006, 1085
96. Russ. Chem. Bull., Int. Ed., 2006, 55, 1126.
97. J. C. Finke, Ph.D. Thesis, Ruhr-University of Bochum, Bochum, 2010, 286 pp.
98. S. V. Chapyshev, Abstrs V Intern. Conf. "High-Spin Molecules and Molecular Magnets" (N. Novgorod, 31 August - 2 September, 2010), N. Novgorod, 2010, O-7.
99. S. V. Chapyshev, R. Walton, J. A. Sanborn, P. M. Lahti, J. Am. Chem. Soc., 2000, 122, 1580.
100. S. V. Chapyshev, R. Walton, P. M. Lahti, Mendeleev Commun., 2000, 138.
101. S. V. Chapyshev, R. Walton, P. M. Lahti, Mendeleev Commun., 2000, 114.
102. S. V. Chapyshev, P. R. Serwinski, Mendeleev Commun., 2001, 92.
103. S. V. Chapyshev, R. Walton, P. R. Serwinski, P. M. Lahti, J. Phys. Chem. A., 2004, 108, 6643.
104. S. V. Chapyshev, P. M. Lahti, J. Phys. Org. Chem., 2006, 19, 637.
105. S. V. Chapyshev, Izv. Akad. Nauk, Ser. Khim., 2006, 1536
106. Russ. Chem. Bull., Int. Ed., 2006, 55, 1593.
107. S. V. Chapyshev, P. Neuhaus, D. Grote, W. Sander, Abstrs of 30th Intern. Symp. on Free Radicals (Savonlinna, 25 - 30 July, 2009), Helsinki, 2009, 103.
108. E. Ya. Misochko, A. V. Akimov, V. F. Lavitskii, S. V. Chapyshev, Izv. Akad. Nauk, Ser. Khim., 2007, 2284
109. Russ. Chem. Bull., Int. Ed., 2007, 56, 2364.
110. E. Ya. Misochko, A. V. Akimov, S. V. Chapyshev, J. Chem. Phys., 2008, 128, 124504.
111. E. Ya. Misochko, A. V. Akimov, S. V. Chapyshev, J. Chem. Phys., 2008, 129, 174510.
112. S. V. Chapyshev, D. Grote, C. Finke, W. Sander, J. Org. Chem., 2008, 73, 7045.
113. S. V. Chapyshev, Zh. Fiz. Khim., 2009, 83, 322
114. Russ. J. Phys. Chem. A (Engl. Transl.), 2009, 83, 254.
115. S. V. Chapyshev, P. Neuhaus, D. Grote, W. Sander, J. Phys. Org. Chem., 2010, 23, 340.
116. E. Ya. Misochko, D. V. Korchagin, K. V. Bozhenko, S. V. Chapyshev, S. M. Aldoshin, J. Chem. Phys., 2010, 133, 064101.
117. S. V. Chapyshev, D. V. Korchagin, V Vseross. nauchn. konf.-shkoly "Vysokoreaktsionnye intermediaty khimicheskikh reaktsii" [V All-Russian Scientific Workshop Conf. "Highly Reactive Intermediates of Chemical Reactions"] (Moscow Region, October 11 - 14, 2010), Moscow, 2010, p. 78 (in Russian).
118. R. B. Morgunov, V. L. Berdinskii, M. V. Kirman, I. Tanimoto, S. V. Chapyshev, Khim. Vysokikh Energii, 2007, 41, 37
119. High Energy Chem. (Engl. Transl.), 2007, 41, 33.
120. L. Mahe, A. Izuoka, T. Sugawara, Bull. Chem. Soc. Jpn, 1998, 71, 1259.
121. S. V. Chapyshev, V. F. Lavitskii, A. V. Akimov, E. Ya. Misochko, A. V. Shastin, D. V. Korchagin, G. V. Shilov, S. M. Aldoshin, Izv. Akad. Nauk, Ser. Khim., 2008, 513
122. Russ. Chem. Bull., Int. Ed., 2008, 57, 524.
123. S. V. Chapyshev, Sovremennye Problemy Organicheskoi Khimii (Modern Problems of Organic Chemistry), Ed. R. R. Kostikov, M. A. Kuznetsov, M. S. Berd, Lem, St.-Petersburg, 2010, issue 15, 121 (in Russian).
124. K. Sugisaki, K. Toyota, K. Sato, D. Shiomi, T. Takui, Angew. Chem., Int. Ed., 2006, 45, 2257.
125. S. V. Chapyshev, Mendeleev Commun., 2002, 168.