First synthesis and investigation of two hydroxyalkyl-substituted 2-tetrazenes

European Journal of Organic Chemistry

Volumn , Issue 7, 1998, Pages 1431-1440

  Porath, Bernd ^a   Münzenberg, Ralf ^a   Heymanns, Peter ^a,b   Rademacher, Paul ^a   Boese, Roland ^a   Bläser, Dieter ^a   Latz, Rüdiger ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b SANOFI   (France)

Author keywords

Ab initio calculations; Hydrogen bonds; NMR spectroscopy; Thermolysis; Transition states

Indexed keywords

EID: 0010001742     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199807)1998:7<1431::AID-EJOC1431>3.0.CO;2-M     Document Type: Article

References (60)

1. F. R. Benson, The High Nitrogen Compounds, Wiley, New York, 1984.
2. S. F. Lang-Fugmann in Methoden der Organischen Chemie (Houben-Weyl), Vol. E16a/2 (Ed.: D. Klamann), Georg Thieme Verlag, Stuttgart, 1990, pp. 1228-1242.
3. E. Enders in Methoden der Organischen Chemie (Houben-Weyl), 4th ed., Vol. 10/2 (Ed.: R. Stroh), Georg Thieme Verlag, Stuttgart, 1967, pp. 508-509.
4. E. Müller in Methoden der Organischen Chemie (Houben-Weyl), 4th ed., Vol. 10/2 (Ed.: R. Stroh), Georg Thieme Verlag, Stuttgart, 1967, p. 828-835.
5. P. Bischof, R. Gleiter, R. Dach, D. Enders, D. Seebach, Tetrahedron 1975, 31, 1415-1417.
6. P. Rademacher, P. Heymanns, R. Carrie, B. Carboni, J. Mol. Struct. 1988, 175, 423-428.
7. P. Heymanns, P. Rademacher, Tetrahedron, 1986, 42, 2511-2518.
8. P. Rademacher, P. Heymanns, R. Münzenberg, H. Wöll, K. Kowski, R. Poppek, Chem. Ber. 1994, 127, 2073-2079.
9. H. Bock, I. Göbel, C. Näther, B. Solouki, A. John, Chem. Ber. 1994, 127, 2197-2208.
10. E. Fischer, Liebigs Ann. Chem. 1878, 190, 67-183.
11. W. C. Danen, F. A. Neugebauer, Angew. Chem. 1975, 87, 823-850; Angew. Chem. Int. Ed. Engl. 1975, 14, 783.
12. W. C. Danen, F. A. Neugebauer, Angew. Chem. 1975, 87, 823-850; Angew. Chem. Int. Ed. Engl. 1975, 14, 783.
13. J. E. Esker, M. Newcomb, Advan. Heterocycl. Chem. 1993, 58, 1-45.
14. N. Wiberg, H. Bachhuber, H. Bayer, Angew. Chem. 1975, 87, 202-203; Angew. Chem. Int. Ed. Engl. 1975, 14, 177.
15. N. Wiberg, H. Bachhuber, H. Bayer, Angew. Chem. 1975, 87, 202-203; Angew. Chem. Int. Ed. Engl. 1975, 14, 177.
16. J. Seetula, K. Kalliorinne, J. Koskikallio, J. Photochem. Photobiol. 1988, 43, 31-41.
17. A. Awadallah, K. Kowski, P. Rademacher, J. Chem. Res. 1996, (S) 437; (M) 2610-2622.
18. S. F. Nelsen in Nitrogen centred radicals (Ed.: J.K. Kochi), Wiley, New York, 1973, chapter 21.
19. S. F. Nelsen, D. H. Heath, J. Am. Chem. Soc. 1969, 91, 6452-6456.
20. J. Hollaender, W. P. Neumann, H. Lind, Chem. Ber. 1973, 106, 2395-2407.
21. T. Weber, J. P. Edwards, S. E. Denmark, Synlett, 1989, 1, 20-22.
22. [20a] G. C. Levy, R. L. Lichter, Nitrogen-15 nuclear magnetic resonance spectroscopy, Wiley, New York, 1979.
23. [20b] W. von Philipsborn, R. Müller, Angew. Chem. 1986, 98, 381-412, Angew. Chem. Int. Ed. Engl. 1986, 25, 383.
24. [20b] W. von Philipsborn, R. Müller, Angew. Chem. 1986, 98, 381-412, Angew. Chem. Int. Ed. Engl. 1986, 25, 383.
25. [20c] S. Berger, S. Braun, H.-O. Kalinowski, NMR Spektroskopie von Nichtmetallen, vol. 2, Georg Thieme Verlag, Stuttgart, 1992.
26. [20d] M. Witanowski, L. Stefaniak, G.A. Webb, Ann. Rep. NMR Spectrosc., 1993, 25, 1-480.
27. B. Rose, D. Schollmeyer, H. Meier, Liebigs Ann. Chem. 1997, 409-412.
28. G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer-Verlag, Berlin, 1994.
29. F. Hibbert, J. Emsley, Advan. Phys. Org Chem. 1990, 26, 255-379.
30. G. S. Hammond, B. Seidel, R. E. Pincock, J. Org. Chem. 1963, 28, 3275-3279.
31. L. J. Madgzinski, K. S. Pillay, H. Richard, Y. L. Chow, Can. J. Chem. 1978, 56, 1657-1667.
32. K. Kimura, S. Katsumata, Y. Achiba, T. Yamazaki, S. Iwata, Handbook of Hel Photoelectron Spectra of Fundamental Organic Molecules, Japan Scientific Societies Press, Tokyo, 1981.
33. M. Veith, G. Schlemmer, Z. Anorg. Allg. Chem. 1982, 494, 7-19.
34. S. F. Nelsen, R. T. I. Landis, J. C. Calabrese, J. Org. Chem. 1977, 42, 4192-4197.
35. P. Heymanns, Elektronische Struktur, Synthese und Thermolyse von 2-Tetrazenen, Dissertation, Universität GH Essen, 1987.
36. P. S. Engel, Chem. Rev. 1980, 80, 99-150.
37. W. Adam, T. Oppenländer, Angew. Chem. 1986, 98, 659-670; Angew. Chem. Int. Ed. Engl. 1986, 25, 661-672.
38. W. Adam, T. Oppenländer, Angew. Chem. 1986, 98, 659-670; Angew. Chem. Int. Ed. Engl. 1986, 25, 661-672.
39. J. S. Adams, K. A. Burton, B. K. Andrews, R. B. Weisman, P. S. Engel, J. Am. Chem. Soc. 1986, 108, 7935-7938.
40. M. Schmittel, C. Rüchardt, J Am. Chem. Soc. 1987, 109, 2750-2759.
41. R. Liu, Q. Cui, K. M. Dunn, K. Morokuma, J. Chem. Phys. 1996, 105, 2333-2345.
42. B. G. Gowenlock, P. P. Jones, D. R. Snelling, Canad. J. Chem. 1963, 41, 1911-1918.
43. F. Lübbe, K.-P. Grosz, W. Hillebrand, W. Sucrow, Tetrahedron Lett. 1981, 22, 227-228.
44. K. Sugiyama, T. Oda, T. Maeshima, Makromol. Chem. 1982, 183, 2445-2452.
45. J. R. Roberts, K. U. Ingold, J Am. Chem. Soc. 1973, 95, 3228-3235.
46. J. J. P. Stewart, J. Comp. Chem 1989, 10, 209-220, 221-264.
47. M. J. S. Dewar, E. G. Zoebisch, H. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
48. J. J. P. Stewart, QCPE No 455, 1983.
49. W. J. Hehre, L. Radom, P. V. R. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York, 1986.
50. [43a] A. D. Becke, J. chem. Phys 1993, 98, 5648-5652.
51. [43b] C. Lee, W. Yang and R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
52. Gaussian 94, Revision C.3, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1995.
53. D. T. Cromer, D. Liberman, J. Chem. Phys. 1970, 53, 1891-1898.
54. G. M. Sheldrick, SHELXTL-PLUS, Version 3.4, Göttingen, 1988.
55. B. L. Mil'man, A. A. Potekhin, Khim. Geterosikl. Soedin. 1973, 7, russ.: 902-907, engl.: 830-834 [Chem. Abs. 1973, 79, 115540z].
56. B. L. Mil'man, A. A. Potekhin, Khim. Geterosikl. Soedin. 1973, 7, russ.: 902-907, engl.: 830-834 [Chem. Abs. 1973, 79, 115540z].
57. H. H. Hatt, Org. Synth. 1943, Coll. Vol. 2, 211-213.
58. J. B. Lambert, J. L. Gosnell, D. S. Bailey, B. M. Henkin, J. Org. Chem. 1969, 34, 4147-4150.
59. R. F. Evans, J. I. Jones, W. Kynaston, J. Chem. Soc. 1963, 4023-4031.
60. E. L. Buhle, A. M. Moore, F. Y. Wiselogle, J. Am. Chem. Soc. 1943, 65, 29.