Gas Phase Thermolysis of Pyrazolines. 5. Electronic Structure and Gas Phase Thermolysis of Tetrazole Derivatives Studied by Photoelectron Spectroscopy

Journal of Heterocyclic Chemistry

Volumn 34, Issue 1, 1997, Pages 113-122

  Awadallah, Adel ^a   Kowski, Klaus ^a   Rademacher, Paul ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000789724     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340119     Document Type: Article

References (72)

1. P. S. Engle, Chem. Rev., 80, 99 (1980).
2. W. Adam and O. De Lucchi, Angew. Chem., 92, 815 (1980); Angew. Chem., Int. Ed. Engl., 19, 762 (1980).
3. W. Adam and O. De Lucchi, Angew. Chem., 92, 815 (1980); Angew. Chem., Int. Ed. Engl., 19, 762 (1980).
4. H. Quast and L. Bieber, Angew. Chem., 87, 422 (1975); Angew. Chem., Int. Ed. Engl., 14, 428 (1975); H. Quast and L. Bieber, Chem. Ber., 114, 325 (1981); H. Quast and U. Nahr, Chem. Ber., 118, 526 (1985); I. R. Dunkln, C. J. Shields, and H. Quast, Tetrahedron, 45, 259 (1989).
5. H. Quast and L. Bieber, Angew. Chem., 87, 422 (1975); Angew. Chem., Int. Ed. Engl., 14, 428 (1975); H. Quast and L. Bieber, Chem. Ber., 114, 325 (1981); H. Quast and U. Nahr, Chem. Ber., 118, 526 (1985); I. R. Dunkln, C. J. Shields, and H. Quast, Tetrahedron, 45, 259 (1989).
6. H. Quast and L. Bieber, Angew. Chem., 87, 422 (1975); Angew. Chem., Int. Ed. Engl., 14, 428 (1975); H. Quast and L. Bieber, Chem. Ber., 114, 325 (1981); H. Quast and U. Nahr, Chem. Ber., 118, 526 (1985); I. R. Dunkln, C. J. Shields, and H. Quast, Tetrahedron, 45, 259 (1989).
7. H. Quast and L. Bieber, Angew. Chem., 87, 422 (1975); Angew. Chem., Int. Ed. Engl., 14, 428 (1975); H. Quast and L. Bieber, Chem. Ber., 114, 325 (1981); H. Quast and U. Nahr, Chem. Ber., 118, 526 (1985); I. R. Dunkln, C. J. Shields, and H. Quast, Tetrahedron, 45, 259 (1989).
8. H. Quast and L. Bieber, Angew. Chem., 87, 422 (1975); Angew. Chem., Int. Ed. Engl., 14, 428 (1975); H. Quast and L. Bieber, Chem. Ber., 114, 325 (1981); H. Quast and U. Nahr, Chem. Ber., 118, 526 (1985); I. R. Dunkln, C. J. Shields, and H. Quast, Tetrahedron, 45, 259 (1989).
9. M. K. Kindermann, R. Poppek, P. Rademacher, A. Fuß and H. Quast, Chem. Ber., 123, 1161 (1990).
10. M. K. Kindermann, K. Kowski, H. M. Muchall, and P. Rademacher, Chem. Ber., 126, 2675 (1993).
11. H. M. Muchall, K. Kowski, P. Rademacher, A. Fuss, R. Neuberger, H. Quast, P. Komnick and W. Sander, Tetrahedron, 52, 1965 (1996).
12. M. K. Kindermann, K. Kowski, P. Rademacher, and H. Quast, Chem. Ber., 126, 2683 (1993).
13. P. Rademacher, B. Carboni, R. Carrié, P. Heymanns, and R. Poppek, Chem. Ber., 121, 1213 (1988); P. Rademacher, P. Heymanns, R. Carrié, and B. Carboni, J. Mol. Struct., 175, 423 (1988).
14. P. Rademacher, B. Carboni, R. Carrié, P. Heymanns, and R. Poppek, Chem. Ber., 121, 1213 (1988); P. Rademacher, P. Heymanns, R. Carrié, and B. Carboni, J. Mol. Struct., 175, 423 (1988).
15. T. Koopmans, Physica, 1, 104 (1934).
16. J. J. P. Stewart, J. Comput. Chem., 10, 209 (1989).
17. S. Cradock, R. H. Findlay, and M. H. Palmer, Tetrahedron, 29, 2173 (1973).
18. M. H. Palmer, I. Simpson, and J. R. Wheeler, Z. Naturforsch., 36A, 1246 (1981).
19. A. Razynska, A. Tempczyk, E. Malinski, J. Szafranek, Z. Grzonka, and P. Hermann, J. Chem. Soc., Perkin Trans. 2, 379 (1983).
20. G. Maier, J. Eckwert, A. Bothur, H. P. Reisenauer, and C. Schmidt, Liebigs Ann. Chem., 1041 (1996).
21. K. Kimura, S. Katsumata, Y. Achiba, T. Yamazaki, and S. Itawa, Handhook of He-I Photoelectron Spectra of Fundamental Organic Molecules, Japan Scientific Societies Press, Tokyo, Halsted Press, New York, 1981.
22. R. Gleiter, T. Veszprémi, and H. Quast, Chem. Ber., 122, 985 (1989).
23. A. D. Becke, J. Chem. Phys., 98, 5648 (1993); C. Lee, W. Yang and R. G. Parr, Phys. Rev. 3, 37, 785 (1988).
24. A. D. Becke, J. Chem. Phys., 98, 5648 (1993); C. Lee, W. Yang and R. G. Parr, Phys. Rev. 3, 37, 785 (1988).
25. H. M. Muchall and P. Rademacher, to be published.
26. H. Bock and B. Solouki, Angew. Chem., 93, 425 (1981); Angew. Chem., Int. Ed. Engl., 20, 427 (1981).
27. H. Bock and B. Solouki, Angew. Chem., 93, 425 (1981); Angew. Chem., Int. Ed. Engl., 20, 427 (1981).
28. R. Schulz and A. Schweig, in Structure and Reactivity, J. L. Liebman and A. Greenberg, eds., VCH Publishers, New York, 1988.
29. H. Meier, W. Heinzelmann, and H. Heimgartner, Chimia, 34, 504, 506 (1980); N. H. Toubro and A. Holm, J. Am. Chem. Soc., 102, 2093 (1980).
30. H. Meier, W. Heinzelmann, and H. Heimgartner, Chimia, 34, 504, 506 (1980); N. H. Toubro and A. Holm, J. Am. Chem. Soc., 102, 2093 (1980).
31. C. Wentrup, S. Fischer, A. Maquestiau and R. Flammang, Angew. Chem., 97, 74 (1985); A ngew. Chem., Int. Ed. Engl., 24, 56 (1985); H. Bock, R. Dammel, S. Fischer, C. Wentrup, Tetrahedron Letters, 28, 617 (1987).
32. C. Wentrup, S. Fischer, A. Maquestiau and R. Flammang, Angew. Chem., 97, 74 (1985); A ngew. Chem., Int. Ed. Engl., 24, 56 (1985); H. Bock, R. Dammel, S. Fischer, C. Wentrup, Tetrahedron Letters, 28, 617 (1987).
33. C. Wentrup, S. Fischer, A. Maquestiau and R. Flammang, Angew. Chem., 97, 74 (1985); A ngew. Chem., Int. Ed. Engl., 24, 56 (1985); H. Bock, R. Dammel, S. Fischer, C. Wentrup, Tetrahedron Letters, 28, 617 (1987).
34. C. Guimon, S. Khayar, F. Gracian, M. Begtrup, and G. Pfister-Guillouzo, Chem. Phys., 138, 157 (1989).
35. T. Koenig, T. Balle, and W. Snell, J. Am. Chem. Soc., 97, 662 (1975).
36. S. Cradock, E. A. V. Ebsworth and J. D. Murdoch, J. Chem. Soc., Faraday Trans. 2, 68, 86 (1972).
37. J. H. D. Eland, Phil. Trans. Roy. Soc. London A, 268, 87 (1970).
38. B. Solouki, P. Rosmus, and H. Bock, J. Am. Chem. Soc., 98, 6054 (1976).
39. H. W. Kroto and R. Suffolk, Chem. Phys. Letters, 15, 545 (1972).
40. J. Bastide and J. P. Maier, Chem. Phys., 12, 177 (1976).
41. D. C. Frost, F. G. Herring, A. Katrib, and C. A. McDowell, Chem. Phys. Letters, 20, 401 (1973).
42. T. Hirabayashi, S. Mohmand, and H. Bock, Chem. Ber., 115, 483 (1982).
43. B. J. M. Neijzen and C. A. De Lange, J. Electr. Spectrosc. Relat. Phenom., 18, 179 (1980).
44. T. Kobayashi and S. Nagakura, J. Electr. Spectrosc. Relat. Phenom., 7, 488 (1975).
45. H. Bock, R. Dammel, and L. Horner, Chem. Ber., 114, 220 (1981); H. Bock and R. Dammel, Angew. Chem., 99, 518 (1987); Angew. Chem., Int. Ed. Engl., 26, 504 (1987).
46. H. Bock, R. Dammel, and L. Horner, Chem. Ber., 114, 220 (1981); H. Bock and R. Dammel, Angew. Chem., 99, 518 (1987); Angew. Chem., Int. Ed. Engl., 26, 504 (1987).
47. H. Bock, R. Dammel, and L. Horner, Chem. Ber., 114, 220 (1981); H. Bock and R. Dammel, Angew. Chem., 99, 518 (1987); Angew. Chem., Int. Ed. Engl., 26, 504 (1987).
48. NIST Standard Reference Database 25, Structures and Properties, version 2.02, National Institute of Standards and Technology, Gaithersburg, Maryland, 1994.
49. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons, London, 1976.
50. A. Rauk, Orbital Interaction Theory of Organic Chemistry, Wiley, New York, 1994.
51. G. Klopman, J. Am. Chem. Soc., 90, 223 (1968).
52. L. Salem, J. Am. Chem. Soc., 90, 543 (1968).
53. J. M. Dyke, L. Golob, N. Jonathan, and A. Morris, J. Chem. Soc., Faraday Trans. 2, 71, 1026 (1975); J. Berkowitz, J. Chem. Phys., 62, 4074 (1975).
54. J. M. Dyke, L. Golob, N. Jonathan, and A. Morris, J. Chem. Soc., Faraday Trans. 2, 71, 1026 (1975); J. Berkowitz, J. Chem. Phys., 62, 4074 (1975).
55. J. W. Bevan, C. Sandorfy, F. Pang, and J. E. Boggs, Spectrochim. Acta, 37A, 601 (1981); L. Asbrink, W. von Niessen, and G. Bieri, J. Electr. Spectrosc. Relat. Phenom., 21, 93 (1980).
56. J. W. Bevan, C. Sandorfy, F. Pang, and J. E. Boggs, Spectrochim. Acta, 37A, 601 (1981); L. Asbrink, W. von Niessen, and G. Bieri, J. Electr. Spectrosc. Relat. Phenom., 21, 93 (1980).
57. R. F. C. Brown, Pyrolytic Methods in Organic Chemistry, Academic Press, New York, 1980.
58. A. Schouten and A. Oskam, Inorg. Chim. Acta, 22, 149 (1977).
59. J. Okubo, H. Ito, T. Hoshi, and T. Kobayashi, Tetrahedron Letters, 26, 643 (1985).
60. J. J. P. Stewart, Quantum Chem. Progr. Exchange No. 455, Department of Chemistry, Indiana University, Bloomington, Indiana, USA.
61. Gaussian 94, Revision B. 1. 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. Defress, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1995.
62. N. L. Allinger, J. Am. Chem. Soc., 99, 8127 (1977).
63. R. Stollé and G. Adam, Ber., 57, 1656 (1924).
64. M. Freund and T. Paradies, Ber., 34, 3110 (1901).
65. A. Awadallah, P. Rademacher, and R. Boese, J. Prakt. Chem., 337, 636 (1995); A. Awadallah, Dissertation, University of Essen, 1995.
66. A. Awadallah, P. Rademacher, and R. Boese, J. Prakt. Chem., 337, 636 (1995); A. Awadallah, Dissertation, University of Essen, 1995.
67. J. P. Horwitz, B. E. Fisher, and A. J. Tomasewski, J. Am. Chem. Soc., 81, 3076 (1959).
68. F. Janssens, J. Torremans and P. A. J. Janssen, J. Med. Chem., 29, 2290 (1986).
69. N. W. Rokke, J. J. Worman, and W. S. Wadsworih. J. Heterocyclic Chem., 12, 1031 (1975).
70. W. S. Wadsworth, J. Org. Chem., 34, 2994 (1969).
71. E. Lieber and J. Ramachandran, Can. J. Chem., 37, 101 (1959).
72. T. Tsuji, H. Satoh, M. Narisada, Y. Hamashima, and T. Yoshida, J. Antibiot., 38, 466 (1985).