Photochemical transformation, 83. - Proximate, syn-periplanar bisdiazene skeletons: Syntheses, structures, homoconjugate reactivity and photochemistry

European Journal of Organic Chemistry

Volumn , Issue 5, 2000, Pages 763-785

  Exner, Kai ^a   Fischer, Gerhard ^a   Bahr, Nikolaus ^a   Beckmann, Eberhard ^a   Lugan, Meinrad ^a   Yang, Fushun ^a   Rihs, Grety ^a   Keller, Manfred ^a   Hunkler, Dieter ^a   Knothe, Lothar ^a   Prinzbach, Horst ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Bisdiazenes; Diazenes; Heterocycles; Homoconjugation; Photochemistry

Indexed keywords

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; ISOMERISM; PHOTOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034051707     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200003)2000:5<763::aid-ejoc763>3.0.co;2-a     Document Type: Article

References (108)

1. G. Fischer, H. Fritz, G. Rihs, D. Hunkler, K. Exner, L. Knothe, H. Prinzbach, Eur. J. Org.Chem. 2000, 743-762, and cit. ref.
2. 4): J. S. Wright, J. Am. Chem. Soc. 1974, 96, 4753-4760.; Cf. B. M. Gimarc, M. Zhao, Inorg. Chem. 1996, 35, 3289-3297.; The assignment of a tetrabenzyltetrazetidine (E. P. Nakova, O. N. Tolkachev, R. P. Evstineva, J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 2660-2663) cannot be correct. The 1,2,3,4-tetrakis(trifluoromethylsulfonyl)-tetrazetidine (A. Haas, R. Walz, Chem. Ber. 1985, 118, 3248-3257) has been corrected (A. Haas, private communication).
3. 4): J. S. Wright, J. Am. Chem. Soc. 1974, 96, 4753-4760.; Cf. B. M. Gimarc, M. Zhao, Inorg. Chem. 1996, 35, 3289-3297.; The assignment of a tetrabenzyltetrazetidine (E. P. Nakova, O. N. Tolkachev, R. P. Evstineva, J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 2660-2663) cannot be correct. The 1,2,3,4-tetrakis(trifluoromethylsulfonyl)-tetrazetidine (A. Haas, R. Walz, Chem. Ber. 1985, 118, 3248-3257) has been corrected (A. Haas, private communication).
4. 4): J. S. Wright, J. Am. Chem. Soc. 1974, 96, 4753-4760.; Cf. B. M. Gimarc, M. Zhao, Inorg. Chem. 1996, 35, 3289-3297.; The assignment of a tetrabenzyltetrazetidine (E. P. Nakova, O. N. Tolkachev, R. P. Evstineva, J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 2660-2663) cannot be correct. The 1,2,3,4-tetrakis(trifluoromethylsulfonyl)-tetrazetidine (A. Haas, R. Walz, Chem. Ber. 1985, 118, 3248-3257) has been corrected (A. Haas, private communication).
5. 4): J. S. Wright, J. Am. Chem. Soc. 1974, 96, 4753-4760.; Cf. B. M. Gimarc, M. Zhao, Inorg. Chem. 1996, 35, 3289-3297.; The assignment of a tetrabenzyltetrazetidine (E. P. Nakova, O. N. Tolkachev, R. P. Evstineva, J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 2660-2663) cannot be correct. The 1,2,3,4-tetrakis(trifluoromethylsulfonyl)-tetrazetidine (A. Haas, R. Walz, Chem. Ber. 1985, 118, 3248-3257) has been corrected (A. Haas, private communication).
6. 4): J. S. Wright, J. Am. Chem. Soc. 1974, 96, 4753-4760.; Cf. B. M. Gimarc, M. Zhao, Inorg. Chem. 1996, 35, 3289-3297.; The assignment of a tetrabenzyltetrazetidine (E. P. Nakova, O. N. Tolkachev, R. P. Evstineva, J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 2660-2663) cannot be correct. The 1,2,3,4-tetrakis(trifluoromethylsulfonyl)-tetrazetidine (A. Haas, R. Walz, Chem. Ber. 1985, 118, 3248-3257) has been corrected (A. Haas, private communication).
7. 4): J. S. Wright, J. Am. Chem. Soc. 1974, 96, 4753-4760.; Cf. B. M. Gimarc, M. Zhao, Inorg. Chem. 1996, 35, 3289-3297.; The assignment of a tetrabenzyltetrazetidine (E. P. Nakova, O. N. Tolkachev, R. P. Evstineva, J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 2660-2663) cannot be correct. The 1,2,3,4-tetrakis(trifluoromethylsulfonyl)-tetrazetidine (A. Haas, R. Walz, Chem. Ber. 1985, 118, 3248-3257) has been corrected (A. Haas, private communication).
8. 4) surfaced as the second least stable isomer: G. Ritter, G. Häfelinger, E. Lüdecke, H. Rau, J. Am. Chem. Soc. 1989, 111, 4627-4635; cf. E. Tauer, R. Marchinek, Liebigs Ann. 1996, 1213-1216.
9. 4) surfaced as the second least stable isomer: G. Ritter, G. Häfelinger, E. Lüdecke, H. Rau, J. Am. Chem. Soc. 1989, 111, 4627-4635; cf. E. Tauer, R. Marchinek, Liebigs Ann. 1996, 1213-1216.
10. [4a] H. Prinzbach, G. Fischer, G. Rihs, G. Sedelmeier, E. Heilbronner, Z.-z. Yang, Tetrahedron Lett. 1982, 23, 1251-1255. -
11. [4b] G. Fischer, D. Hunkler, H. Prinzbach, G. Rihs, H. Fritz, Tetrahedron Lett. 1984, 25, 2459-2462. -
12. [4c] H. Fritz, G. Fischer, W. Marterer, H. Prinzbach, Tetrahedron Lett. 1985, 26, 4427-4430. -
13. [4d] G. Fischer, G. Sedelmeier, H. Prinzbach, K. Knoll, P. Wilharm, G. Huttner, I. Jibril, J. Organomet. Chem. 1985, 297, 307-312. -
14. [4e] W. Marterer, H. Fritz, H. Prinzbach, Tetrahedron Lett. 1987, 28, 5497-5500. -
15. [4f] R. Gleiter, C. Sigwart, H. Irngartinger, S. Gries, W. Marterer, O. Klingler, H. Prinzbach, Tetrahedron Lett. 1988, 29, 185-188.
16. [4g] W Marterer, H. Prinzbach, G. Rihs, J. Wirz, J. Lecoultre, E. Heilbronner, Helvetica Chim. Acta 1988, 71, 1937-1965. -
17. [4h] E. Beckmann, N. Bahr, H. Prinzbach, G. Rihs, Tetrahedron Lett. 1990, 31, 1125-1128. -
18. [4i] N. Bahr, E. Beckmann, K. Mathauer, D. Hunkler, M. Keller, H. Prinzbach, H. Vahrenkamp, Chem. Ber. 1993, 126, 429-440. -
19. [4k] K. Exner, D. Hochstrate, M. Keller, F.-G. Klärner, H. Prinzbach. Angew. Chem. 1996, 108, 2399-2402; Angew. Chem. Int. Ed. 1996, 35, 2256-2259. -
20. [4k] K. Exner, D. Hochstrate, M. Keller, F.-G. Klärner, H. Prinzbach. Angew. Chem. 1996, 108, 2399-2402; Angew. Chem. Int. Ed. 1996, 35, 2256-2259. -
21. [4l] O. Cullmann, M. Vögtle, F. Stelzer, H. Prinzbach, Tetrahedron Lett. 1998, 39, 2303-2306. -
22. [4m] K. Exner, H. Prinzbach. Chem. Commun. 1998, 749-750.
23. [5a] G. Fischer, Diplomarbeit, 1981, Dissertation, University of Freiburg, 1987. -
24. [5a] G. Fischer, Diplomarbeit, 1981, Dissertation, University of Freiburg, 1987. -
25. [5b] K. Mathauer, Diplomarbeit, University of Freiburg, 1989. -
26. [5c] E. Beckmann, Dissertation, University of Freiburg, 1991. -
27. [5d] N. Bahr, Dissertation, University of Freiburg, 1994. -
28. [5e] M. Lugan, Dissertation, University of Freiburg, 1994. -
29. [5f] O. Cullmann, Dissertation, University of Freiburg, 1998. -
30. [5g] K. Exner, Dissertation, University of Freiburg, 1998. -
31. [5h] M. Vogtle, Dissertation, University of Freiburg, in preparation.
32. For the early synthesis of proximate bisdiazenes built upon a bicyclo[3.3.1]nonane skeleton see J. M. Mellor, N. M. Smith, J. Chem. Res. Synop. 1985, 60.; J. M. Mellor, R. Pathirana, N. M. Smith, J. Chem. Soc., Perkin I, 1988, 2501-2507, and cited references.
33. For the early synthesis of proximate bisdiazenes built upon a bicyclo[3.3.1]nonane skeleton see J. M. Mellor, N. M. Smith, J. Chem. Res. Synop. 1985, 60.; J. M. Mellor, R. Pathirana, N. M. Smith, J. Chem. Soc., Perkin I, 1988, 2501-2507, and cited references.
34. [7a] K. Exner, D. Hunkler, G. Gescheidt, H. Prinzbach, Angew. Chem. 1998, 110, 2013-2016; Angew. Chem. Int. Ed. 1998, 37,1910-1913. -
35. [7a] K. Exner, D. Hunkler, G. Gescheidt, H. Prinzbach, Angew. Chem. 1998, 110, 2013-2016; Angew. Chem. Int. Ed. 1998, 37,1910-1913. -
36. [7b] K. Exner, H. Prinzbach, G. Gescheidt, B. Großmann, J. Heinze, J. Am. Chem. Soc. 1999, 121, 1964-1965. -
37. [7c] K. Exner, B. Großmann, G. Gescheidt, J. Heinze, M. Keller, T. Bally, P. Bednarek, H. Prinzbach, in preparation.
38. D. C. Dong, J. T. Edward, J. Org. Chem. 1980, 45, 2395-2399; and cited references.
39. Cf. ref.[4,9,10] in the preceding paper.; H.-D. Martin, R. Schwesinger, Chem. Ber. 1974, 107, 3143-3145.; G. Sedelmeier, H. Prinzbach, H.-D. Martin, Chimia 1979, 33, 329-332.
40. Cf. ref.[4,9,10] in the preceding paper.; H.-D. Martin, R. Schwesinger, Chem. Ber. 1974, 107, 3143-3145.; G. Sedelmeier, H. Prinzbach, H.-D. Martin, Chimia 1979, 33, 329-332.
41. 22 systems (G. Fischer, E. Beckmann, H. Prinzbach, G. Rihs, J. Wirz, Tetrahedron Lett. 1986, 27, 1273-1276).
42. 22 systems (G. Fischer, E. Beckmann, H. Prinzbach, G. Rihs, J. Wirz, Tetrahedron Lett. 1986, 27, 1273-1276).
43. 22 systems (G. Fischer, E. Beckmann, H. Prinzbach, G. Rihs, J. Wirz, Tetrahedron Lett. 1986, 27, 1273-1276).
44. 22 systems (G. Fischer, E. Beckmann, H. Prinzbach, G. Rihs, J. Wirz, Tetrahedron Lett. 1986, 27, 1273-1276).
45. E. Osawa, K. Aigami, Y. Inamoto, J. Org. Chem. 1977, 42, 2621-2626.
46. K. Exner, G. Fischer, M. Lugan, H. Fritz, D. Hunkler, M. Keller, L. Knothe, H. Prinzbach, Eur. J. Org. Chem. 2000, 787-806.
47. A. Padwa "1,3-Dipolar Cycloaddition Chemistry", Vol. 1,2, Wiley, New York, 1984. The N = N double bond is not particularly known as a π2 component for additions with azomethineimine (R. Grashey, chapter 7), azimine and azoxy dipoles (R. C. Storr, chapter 10).
48. For [3+3]cycloadditions of azomethineimines see E. Schmitz, Chem. Ber. 1958, 91, 1495.; R. Huisgen, R. Grashey, P. Laur, H. Leitermann, Angew. Chem. 1960, 72, 416.
49. For [3+3]cycloadditions of azomethineimines see E. Schmitz, Chem. Ber. 1958, 91, 1495.; R. Huisgen, R. Grashey, P. Laur, H. Leitermann, Angew. Chem. 1960, 72, 416.
50. B. Albert, W. Berning, C. Burschka, S. Hünig, H.-D. Martin, F. Prokschy, Chem. Ber. 1981, 114, 423-432.; K. Beck, S. Hünig, Chem. Ber. 1987, 120, 477-483.; S. Hünig, H.-D. Martin, B. Mayer, K. Peters, F. Prokschy, M. Schmitt, H. G. von Schnerina, Chem. Ber. 1987, 120, 195-201.; U. Brand, S. Hünig, H.-D. Martin, B. Mayer, Liebigs Ann. 1996, 1401-1406.
51. B. Albert, W. Berning, C. Burschka, S. Hünig, H.-D. Martin, F. Prokschy, Chem. Ber. 1981, 114, 423-432.; K. Beck, S. Hünig, Chem. Ber. 1987, 120, 477-483.; S. Hünig, H.-D. Martin, B. Mayer, K. Peters, F. Prokschy, M. Schmitt, H. G. von Schnerina, Chem. Ber. 1987, 120, 195-201.; U. Brand, S. Hünig, H.-D. Martin, B. Mayer, Liebigs Ann. 1996, 1401-1406.
52. B. Albert, W. Berning, C. Burschka, S. Hünig, H.-D. Martin, F. Prokschy, Chem. Ber. 1981, 114, 423-432.; K. Beck, S. Hünig, Chem. Ber. 1987, 120, 477-483.; S. Hünig, H.-D. Martin, B. Mayer, K. Peters, F. Prokschy, M. Schmitt, H. G. von Schnerina, Chem. Ber. 1987, 120, 195-201.; U. Brand, S. Hünig, H.-D. Martin, B. Mayer, Liebigs Ann. 1996, 1401-1406.
53. B. Albert, W. Berning, C. Burschka, S. Hünig, H.-D. Martin, F. Prokschy, Chem. Ber. 1981, 114, 423-432.; K. Beck, S. Hünig, Chem. Ber. 1987, 120, 477-483.; S. Hünig, H.-D. Martin, B. Mayer, K. Peters, F. Prokschy, M. Schmitt, H. G. von Schnerina, Chem. Ber. 1987, 120, 195-201.; U. Brand, S. Hünig, H.-D. Martin, B. Mayer, Liebigs Ann. 1996, 1401-1406.
54. W. Berning, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1455-1464.
55. P. Ashkenazi, D. Ginsburg, E. Vogel, Tetrahedron 1977, 33, 1196.; P. Ashkenazi, D. Ginsburg. Israel J. Chemistry 1989, 29, 281-288.; H. Frauenrath, M. Kapon, M. B. Rubin, Israel J. Chemistrv 1989, 29, 307-310.
56. P. Ashkenazi, D. Ginsburg, E. Vogel, Tetrahedron 1977, 33, 1196.; P. Ashkenazi, D. Ginsburg. Israel J. Chemistry 1989, 29, 281-288.; H. Frauenrath, M. Kapon, M. B. Rubin, Israel J. Chemistrv 1989, 29, 307-310.
57. P. Ashkenazi, D. Ginsburg, E. Vogel, Tetrahedron 1977, 33, 1196.; P. Ashkenazi, D. Ginsburg. Israel J. Chemistry 1989, 29, 281-288.; H. Frauenrath, M. Kapon, M. B. Rubin, Israel J. Chemistrv 1989, 29, 307-310.
58. E. L. Allredt, K. I. Vorehees, J. Am. Chem. Soc. 1973, 95, 620-621.
59. E. Vogel, H. D. Roth, Angew. Chem. 1964, 76, 145.; W. Klug, Dissertation, University of Cologne, 1972.
60. E. Vogel, H. D. Roth, Angew. Chem. 1964, 76, 145.; W. Klug, Dissertation, University of Cologne, 1972.
61. [20a] A. B. Evnin, D. R. Arnold, J. Am. Chem. Soc. 1968, 90, 5330-5332. -
62. [20b] D. R. Arnold, A. B. Evnin, P. H. Kasai, J. Am. Chem. Soc. 1969, 91, 784-785. -
63. [20c] A. B. Evnin, D. R. Arnold, L. A. Karnischky, E. Strom, J. Am. Chem. Soc. 1970, 92, 6218-6231. -
64. [20d] L. A. Paquette, L. M. Leichtner, J. Am. Chem. Soc. 1970, 92, 1765-1766. -
65. [20e] L. A. Paquette, L. M. Leichtner, J. Am. Chem. Soc. 1971, 93, 4922-4924; ibd. 1971, 93, 5128-5136.
66. [20e] L. A. Paquette, L. M. Leichtner, J. Am. Chem. Soc. 1971, 93, 4922-4924; ibd. 1971, 93, 5128-5136.
67. P. A. Grieco, J. J. Nunes, M. D. Gaul, J. Am. Chem. Soc. 1990, 112, 4595-4596.
68. G. Frenzen, C. Gerninghaus, C. Meyer-Bulheimer, E. F. Paulus, G. Seitz, Liebigs Ann. 1995, 1313-1318.; C. Gerninghaus, A. Kümmel, G. Seitz, Chem. Ber. 1993, 126, 733-738.
69. G. Frenzen, C. Gerninghaus, C. Meyer-Bulheimer, E. F. Paulus, G. Seitz, Liebigs Ann. 1995, 1313-1318.; C. Gerninghaus, A. Kümmel, G. Seitz, Chem. Ber. 1993, 126, 733-738.
70. High-pressure Diels-Alder-additions of 16b to nonactivated alkenes are described: K. Beck, S. Hünig, F.-G. Klarner, P. Kraft, U. Artschwager-Perl, Chem. Ber. 1987, 120, 2041-2051; S. Hünig, P. Kraft, F-G. Klärner, U. Artschwager-Perl, K. Peters, H.-G. von Schnering, Liebigs Ann. 1995, 351-356 and cited references.
71. High-pressure Diels-Alder-additions of 16b to nonactivated alkenes are described: K. Beck, S. Hünig, F.-G. Klarner, P. Kraft, U. Artschwager-Perl, Chem. Ber. 1987, 120, 2041-2051; S. Hünig, P. Kraft, F-G. Klärner, U. Artschwager-Perl, K. Peters, H.-G. von Schnering, Liebigs Ann. 1995, 351-356 and cited references.
72. F. D. Greene, S. S. Hecht, Tetrahedron Lett. 1969, 10, 575-578.; H. Olsen, J. Am. Chem. Soc. 1982, 6836-6838.; S. Hünig, M. Schmitt, J. Prakt. Chem. 1996, 338, 74-82.
73. F. D. Greene, S. S. Hecht, Tetrahedron Lett. 1969, 10, 575-578.; H. Olsen, J. Am. Chem. Soc. 1982, 6836-6838.; S. Hünig, M. Schmitt, J. Prakt. Chem. 1996, 338, 74-82.
74. F. D. Greene, S. S. Hecht, Tetrahedron Lett. 1969, 10, 575-578.; H. Olsen, J. Am. Chem. Soc. 1982, 6836-6838.; S. Hünig, M. Schmitt, J. Prakt. Chem. 1996, 338, 74-82.
75. Crystallographic data (excluding structure factors) for the structure(s) reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 133156 (1a), 404417 (2), 118981 (18b), 133334 (25c), 118984 (Rh-complex). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internal.) + 44-1223/ 336-033; E-mail: deposit@ccdc.cam.ac.uk].
76. T. Ottersen, C. Rømming, J. P. Snyder, Acta Chem. Scand. B 1976, 30, 407; P. S. Engel, S. Duan, K. H. Whitmire, J. Org. Chem. 1998, 63, 5666-5667.
77. T. Ottersen, C. Rømming, J. P. Snyder, Acta Chem. Scand. B 1976, 30, 407; P. S. Engel, S. Duan, K. H. Whitmire, J. Org. Chem. 1998, 63, 5666-5667.
78. B. D. Baigrie, H. I. G. Cadogan, J. T. Sharp, J. Chem. Soc., Perkin Trans. 1 1975, 1065.; B. Krumm, A. V. Robert, J. Kirchmeier, J. M. Shreeve, H. Oberhammer, Angew. Chem. 1995, 107, 645-647; Angew. Chem. Int. Ed. Engl. 1995, 34, 586.
79. B. D. Baigrie, H. I. G. Cadogan, J. T. Sharp, J. Chem. Soc., Perkin Trans. 1 1975, 1065.; B. Krumm, A. V. Robert, J. Kirchmeier, J. M. Shreeve, H. Oberhammer, Angew. Chem. 1995, 107, 645-647; Angew. Chem. Int. Ed. Engl. 1995, 34, 586.
80. B. D. Baigrie, H. I. G. Cadogan, J. T. Sharp, J. Chem. Soc., Perkin Trans. 1 1975, 1065.; B. Krumm, A. V. Robert, J. Kirchmeier, J. M. Shreeve, H. Oberhammer, Angew. Chem. 1995, 107, 645-647; Angew. Chem. Int. Ed. Engl. 1995, 34, 586.
81. Cf. P. Hoffman, S. Hünig, L. Waltz, K. Peters, H. G. von Schnering, Tetrahedron 1995, 51, 13197-13216, and cit. ref.
82. Azomethinimines, liberated by thermal fragmentation of hexahydro-1,2,4,5-tetrazines, have been intercepted with azodicarboxylates to give - in modest yields - crystalline, colorless (most probably) persubstituted tetrazolidines. The latter, in acetic media, behave as oxidants towards iodide (R. Grashey, Habilitationsschrift, München 1965; R. Grashey in "1,3-Dipolar Cycloaddition Chemistry" (Ed. A. Padwa) Wiley, New York 1984, p. 733; a similarly stable tetrazolidine was obtained with the isoquinoline-N-phenylimine and bis(tert-butyl)azodicarboxylate (R. Temme, Dissertation, Universität München 1980, S. 99. We thank Prof. R. Huisgen for communicating these results to us. K. Bast, M. Behrens, T. Durst, R. Grashey, R. Huisgen, R. Schiffer, R. Temme, Eur. J. Org. Chem. 1998, 379-386.
83. Azomethinimines, liberated by thermal fragmentation of hexahydro-1,2,4,5-tetrazines, have been intercepted with azodicarboxylates to give - in modest yields - crystalline, colorless (most probably) persubstituted tetrazolidines. The latter, in acetic media, behave as oxidants towards iodide (R. Grashey, Habilitationsschrift, München 1965; R. Grashey in "1,3-Dipolar Cycloaddition Chemistry" (Ed. A. Padwa) Wiley, New York 1984, p. 733; a similarly stable tetrazolidine was obtained with the isoquinoline-N-phenylimine and bis(tert-butyl)azodicarboxylate (R. Temme, Dissertation, Universität München 1980, S. 99. We thank Prof. R. Huisgen for communicating these results to us. K. Bast, M. Behrens, T. Durst, R. Grashey, R. Huisgen, R. Schiffer, R. Temme, Eur. J. Org. Chem. 1998, 379-386.
84. Azomethinimines, liberated by thermal fragmentation of hexahydro-1,2,4,5-tetrazines, have been intercepted with azodicarboxylates to give - in modest yields - crystalline, colorless (most probably) persubstituted tetrazolidines. The latter, in acetic media, behave as oxidants towards iodide (R. Grashey, Habilitationsschrift, München 1965; R. Grashey in "1,3-Dipolar Cycloaddition Chemistry" (Ed. A. Padwa) Wiley, New York 1984, p. 733; a similarly stable tetrazolidine was obtained with the isoquinoline-N-phenylimine and bis(tert-butyl)azodicarboxylate (R. Temme, Dissertation, Universität München 1980, S. 99. We thank Prof. R. Huisgen for communicating these results to us. K. Bast, M. Behrens, T. Durst, R. Grashey, R. Huisgen, R. Schiffer, R. Temme, Eur. J. Org. Chem. 1998, 379-386.
85. Azomethinimines, liberated by thermal fragmentation of hexahydro-1,2,4,5-tetrazines, have been intercepted with azodicarboxylates to give - in modest yields - crystalline, colorless (most probably) persubstituted tetrazolidines. The latter, in acetic media, behave as oxidants towards iodide (R. Grashey, Habilitationsschrift, München 1965; R. Grashey in "1,3-Dipolar Cycloaddition Chemistry" (Ed. A. Padwa) Wiley, New York 1984, p. 733; a similarly stable tetrazolidine was obtained with the isoquinoline-N-phenylimine and bis(tert-butyl)azodicarboxylate (R. Temme, Dissertation, Universität München 1980, S. 99. We thank Prof. R. Huisgen for communicating these results to us. K. Bast, M. Behrens, T. Durst, R. Grashey, R. Huisgen, R. Schiffer, R. Temme, Eur. J. Org. Chem. 1998, 379-386.
86. [7c]
87. [7c] Cf. the X-ray structures of the silaethene-amine adducts: N. Wiberg, K. S. Joz, K. Palborn, Chem. Ber. 1993, 126, 67-69.
88. 15N NMR-Speccopy, in NMR Basic Principles and Progress (Eds. P. Diehl, E. Fluck, E. Korsfeld), Vol. 18, 1981, Springer, Berlin.
89. A. Albini, H. Kisch, Top. Curr. Chem. 1976, 105-142.; H. Kisch. P. Reißer, F. Knoch, Chem. Ber. 1991, 124, 1143-1148.
90. A. Albini, H. Kisch, Top. Curr. Chem. 1976, 105-142.; H. Kisch. P. Reißer, F. Knoch, Chem. Ber. 1991, 124, 1143-1148.
91. A. Albini, H. Kisch, C. Krüger, A. Chiang, Z. Naturforsch. (B) 1982, 37, 463-467; A. Albini, H. Kisch, Z. Naturforsch. (B) 1982, 37, 468-472.
92. A. Albini, H. Kisch, C. Krüger, A. Chiang, Z. Naturforsch. (B) 1982, 37, 463-467; A. Albini, H. Kisch, Z. Naturforsch. (B) 1982, 37, 468-472.
93. H. Rau, Angew. Chem. 1973, 85, 245-258; Angew. Chem. Int. Ed. 1973 12, 224-237.
94. H. Rau, Angew. Chem. 1973, 85, 245-258; Angew. Chem. Int. Ed. 1973 12, 224-237.
95. P. S. Engel, Chem. Rev. 1980, 80, 99.; W. Adam, O. Deluchi, Angew. Chem. 1980, 92, 815-832; Angew. Chem. Int. Ed. 1980, 19, 762.
96. P. S. Engel, Chem. Rev. 1980, 80, 99.; W. Adam, O. Deluchi, Angew. Chem. 1980, 92, 815-832; Angew. Chem. Int. Ed. 1980, 19, 762.
97. P. S. Engel, Chem. Rev. 1980, 80, 99.; W. Adam, O. Deluchi, Angew. Chem. 1980, 92, 815-832; Angew. Chem. Int. Ed. 1980, 19, 762.
98. S. P. Engel, D. W. Horsey, D. E. Keys, C. J. Nalepa, L. R. Soltero, J. Am. Chem. Soc. 1983, 105, 7108-7114.; M. A Anderson, C. B. Grissom, J. Am. Chem. Soc. 1995, 117, 5041-5048.; N. Yamamoto, M. Olivucci, P. Celani, M. A. Robb, J. Am. Chem. Soc. 1998, 120, 2391-2407.
99. S. P. Engel, D. W. Horsey, D. E. Keys, C. J. Nalepa, L. R. Soltero, J. Am. Chem. Soc. 1983, 105, 7108-7114.; M. A Anderson, C. B. Grissom, J. Am. Chem. Soc. 1995, 117, 5041-5048.; N. Yamamoto, M. Olivucci, P. Celani, M. A. Robb, J. Am. Chem. Soc. 1998, 120, 2391-2407.
100. S. P. Engel, D. W. Horsey, D. E. Keys, C. J. Nalepa, L. R. Soltero, J. Am. Chem. Soc. 1983, 105, 7108-7114.; M. A Anderson, C. B. Grissom, J. Am. Chem. Soc. 1995, 117, 5041-5048.; N. Yamamoto, M. Olivucci, P. Celani, M. A. Robb, J. Am. Chem. Soc. 1998, 120, 2391-2407.
101. [38a] O. Klingler, H. Prinzbach, Angew. Chem. 1987, 99, 579-580; Angew. Chem. Int. Ed. Engl. 1987, 26, 566-567. -
102. [38a] O. Klingler, H. Prinzbach, Angew. Chem. 1987, 99, 579-580; Angew. Chem. Int. Ed. Engl. 1987, 26, 566-567. -
103. [38b] W. Marterer, H. Fritz, H. Prinzbach, Tetrahedron Lett. 1987, 28, 5497-5500. -
104. [38c] H. Irngartinger, D. Kallfaß, H. Prinzbach, O. Klingler, Chem. Ber. 1989, 122, 175-178. -
105. [38d] W. Marterer, O. Klingler, R. Thiergardt, E. Beckmann, H. Fritz, H. Prinzbach, Chem. Ber. 1991, 124, 621-633.
106. M. Heitzmann, F. Yang, M. Kegel, H. Prinzbach, in preparation.
107. This protocol was kindly worked out by Prof. Seitz and co-workers.
108. This protocol was kindly worked out by Prof. Klärner and Dr. Hochstrate.