Synthesis of dipolar nitronyl nitroxides

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2269-2270

  Greve, Stefan ^a   Näther, Christian ^a   Friedrichsen, Willy ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005490088     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0060329     Document Type: Article

References (41)

1. Osiecki, J. H.; Ullman, E. F. J. Am. Chem. Soc. 1968, 90, 1078-1079.
2. (a) Miller, J. S. Adv. Mater. 1994, 6, 322-324.
3. (b) Gatteschi, D. Adv. Mater. 1994, 6, 635-645.
4. (c) Nakatsuji, S.; Anzai, H. J. Mater. Chem. 1997, 7, 2161-2174.
5. (d) Plass, W. Chem. Unserer Zeit 1998, 32, 323-333.
6. Turek, P.; Nozawa, K.; Shiomi, D.; Awaga, K.; Inabe, T.; Maruyama, Y.; Kinoshita, M. Chem. Phys. Lett. 1991, 180, 327-331.
7. Recent work: (a) Catala, L.; Turek, P.; Le Moigne, J.; De Cian, A.; Kyritsakas, N. Tetrahedron Lett. 2000, 41, 1015-1018.
8. (b) Félix, O.; Hosseini, M. W.; De Cian, A.; Fischer, J.; Catala, L.; Turek, P. Tetrahedron Lett. 1999, 40, 2943-2946.
9. (c) Alcântara, A. F. C.; Dos Santos, H. F.; De Almeida, W. B.; Vaz, M. G. F.; Pinheiro, L. H. M.; Stumpf, H. O. Struct. Chem. 1999, 10, 637-674.
10. (d) Heise, H.; Köhler, F. H.; Mota, F.; Novoa, J. J.; Veciana, J. J. Am. Chem. Soc. 1999, 121, 9659-9667.
11. (e) Romero, F. M.; Ziessel, R. Tetrahedron Lett. 1999, 40, 1895-1898.
12. (f) Stroh, C.; Turek, P.; Ziessel, R. J. Chem. Soc., Chem. Commun. 1998, 2337-2338.
13. (g) García-Muñoz, J. L.; Cirujeda, J.; Veciana, J.; Cox, S. F. J. Chem. Phys. Lett. 1998, 293, 160-166.
14. (h) Hamachi, K.; Matsuda, K.; Iwamura, H. Bull. Chem. Soc. Jpn. 1998, 71, 2937-2944.
15. (i) Matsushita, M. M.; Izuoka, A.; Sugawara, T.; Kobayashi, T.; Wada, N.; Takeda, N.; Ishikawa, M. J. Am. Chem. Soc. 1997, 119, 4369-4379.
16. (j) Frank, N. L.; Clérac, R.; Sutter, J.-P.; Daro, N.; Kahn, O.; Coulon, C.; Green, M. T.; Golhen, S.; Ouahab, L. J. Am. Chem. Soc. 2000, 122, 2053-2061 and references cited therein.
17. (a) Kinoshita, M. Jpn. J. Appl. Phys. 1994, 33, 5718-5733.
18. (b) Deumal, M.; Cirujeda, J.; Veciana, J.; Novoa, J. J. Adv. Mater. 1998, 10, 1461-1465.
19. 7 of this type have been reported repeatedly.
20. For a definition see: (a) Newton, C. G.; Ramsden, C. A. Tetrahedron 1982, 38, 2965-3011.
21. (b) Ollis, W. D., Stanforth, S. P., Ramsden, C. A. Tetrahedron 1985, 41, 2239-2329.
22. Review: Friedrichsen, W.; Böttcher, A.; Kappe, T. Heterocycles 1982, 19, 1083-1148.
23. Recent work: (a), Kappe, T.; Lube, W.; Thonhofer, K.; Kratky, C.; Wagner, U. G. Heterocycles 1995, 40, 681-690.
24. (b) Abd El-Sayed Issac, Y. Bull. Chem. Soc. Jpn. 1999, 72, 503-509.
25. (c) Potts, K. T.; Rochanapruk, T.; Coates, S. J.; Hadjiarapoglu, L.; Padwa, A. J. Org. Chem. 1993, 58, 5040-5042.
26. 11 as the amount of the corresponding bisacetal was only small.
27. Jpn. Kokai Tokkyo Koho JP 81.156.229 (Dec. 2, 1981); Chem. Abstr. 1982, 96, 142458m.
28. This methodology has been worked out by A.-C. Koch: Ph.D. Dissertation, University of Kiel, 1991.
29. (a) Kappe, T. Encyclopedia of Reagents in Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995; Vol. 1, 557-579.
30. (b) Kappe, T.; Lube, W. Monatsh. Chem. 1971, 102, 781-787.
31. (c) Friedrichsen, W.; Schmidt, R.; van Hummel, G. J.; van den Ham, D. M. W. Liebigs Ann. Chem. 1981, 521-531.
32. On the basis of spectroscopic evidence, including EI-MS. The structures of all new compounds were unequivocally authenticated (see Supporting Information).
33. o). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 145335. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2, 1EZ, U.K. Fax: +44-(0)1223-336033. Email: deposit@ccdc.cam.ac.uk.
34. For crystal structures of 3-aryl(heteroaryl)-substituted nitronyl nitroxides, see, e.g.: (a) Caneschi, A.; Ferraro, F.; Gatteschi, D.; le Lirzin, A.; Novak M. A.; Rentschler, E.; Sessoli, R. Adv. Mater. 1995, 7, 476-478.
35. (b) Akita, T.; Kobayashi, K. Adv. Mater. 1997, 9, 346-349.
36. (c) Zhang, D.; Zhou, W.; Zhu, D. J. Mater. Chem. 1999, 9, 1409-1413.
37. (d) Zheludev, A.; Barone, V.; Bonnet, M.; Delley, B.; Grand, A.; Ressouche, E.; Rey, P.; Subra, R.; Schweizer, J. J. Am. Chem. Soc. 1994, 116, 2019-2027 and ref 4b and 4i.
38. These calculations were performed with the program system MOPAC, version 7.00.
39. Laackmann, P.; Friedrichsen, W. Tetrahedron 1996, 52, 5475-5475.
40. Greve, S.; Friedrichsen, W.; unpublished material. Part of the Ph.D. Dissertation of Greve, S., University of Kiel, 2000.
41. Presented in part at the XIth Winter School on Coordination Chemistry, Karpacz, Poland, 7-11 December 1998: Friedrichsen, W., Greve, S.; Mrozinsky, J.; Skrupa, A.; Pochaba, A.; Naether, C.; Friedrichsen, W., manuscript in preparation.