Reactions of unsaturated azides, 12[≠] azido-1,2,3-triphenylpropenes of varying stabilities: A corrigendum of structure assignment

European Journal of Organic Chemistry

Volumn , Issue 2, 2000, Pages 257-267

  Banert, Klaus ^a   Hagedorn, Manfred ^a   Liedtke, Christine ^b   Melzer, Antje ^a   Schöffler, Claudia ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF SIEGEN   (Germany)

Author keywords

2H Azirines; Allyl azides; Photochemical cis trans isomerizations; Prototropic rearrangements; Sigmatropic rearrangements; Vinyl azides

Indexed keywords

AZIDE; PROPYLENE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR STABILITY; REACTION ANALYSIS;

EID: 0033955119     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200001)2000:2<257::aid-ejoc257>3.0.co;2-r     Document Type: Article

References (102)

1. G. L'abbé, Angew. Chem. 1975, 87, 831-838; Angew. Chem. Int. Ed. Engl. 1975, 14, 775.
2. G. L'abbé, Angew. Chem. 1975, 87, 831-838; Angew. Chem. Int. Ed. Engl. 1975, 14, 775.
3. [2a] G. L'abbé, A. Hassner, Angew. Chem. 1971, 83, 103-109; Angew. Chem. Int. Ed. Engl. 1971, 10, 98-104.
4. [2a] G. L'abbé, A. Hassner, Angew. Chem. 1971, 83, 103-109; Angew. Chem. Int. Ed. Engl. 1971, 10, 98-104.
5. [2b] G. Smolinsky, C. A. Pryde, in The Chemistry of the Azido Group (Ed.: S. Patai), Wiley, London, 1971, pp. 555-585.
6. [2c] A. Hassner, in Azides and Nitrenes: Reactivity and Utility (Ed.: E. F. V. Scriven), Academic Press, Orlando, 1984, pp. 35-94.
7. [2d] K. Banert, in Houben-Weyl, Vol. E 15 (Eds.: H. Kropf, E. Schaumann), Thieme, Stuttgart, 1993, pp. 818-875, 1344-1347, 2348-2349, 3105-3107.
8. [3a] H. Priebe, Angew. Chem. 1984, 96, 728-729; Angew. Chem. Int. Ed. Engl. 1984, 23, 736-737.
9. [3a] H. Priebe, Angew. Chem. 1984, 96, 728-729; Angew. Chem. Int. Ed. Engl. 1984, 23, 736-737.
10. [3b] K. Banert, Angew. Chem. 1985, 97, 231-232; Angew. Chem. Int. Ed. Engl. 1985, 24, 216-217.
11. [3b] K. Banert, Angew. Chem. 1985, 97, 231-232; Angew. Chem. Int. Ed. Engl. 1985, 24, 216-217.
12. [3c] K. Banert, Tetrahedron Lett. 1985, 26, 5261-5264.
13. [3d] S. H. Schei, H. Priebe, C. J. Nielsen, P. Klaeboe, J. Mol. Struct. 1986, 147, 203-215.
14. [3e] C. J. Nielsen, P. Klaeboe, H. Priebe, S. H. Schei, J. Mol. Struct. 1986, 147, 217-229.
15. [3f] K. Banert, Chem. Ber. 1987, 120, 1891-1896.
16. [3g] K. Nishiyama, M. Oba, A. Watanabe, Tetrahedron 1987, 43, 693-700.
17. [3h] K. Banert, Chem. Ber. 1989, 122, 911-918.
18. [3i] K. Banert, M. Hagedorn, Angew. Chem. 1989, 101, 1710-1711; Angew. Chem. Int. Ed. Engl. 1989, 28, 1675-1676.
19. [3i] K. Banert, M. Hagedorn, Angew. Chem. 1989, 101, 1710-1711; Angew. Chem. Int. Ed. Engl. 1989, 28, 1675-1676.
20. [3j] K. Banert, Liebigs Ann./Recueil 1997, 2005-2018.
21. [3k] K. Banert, W. Fendel, J. Schlott, Angew. Chem. 1998, 110, 3488-3491; Angew. Chem. Int. Ed. 1998, 37, 3289-3292.
22. [3k] K. Banert, W. Fendel, J. Schlott, Angew. Chem. 1998, 110, 3488-3491; Angew. Chem. Int. Ed. 1998, 37, 3289-3292.
23. [4a] F. G. Bordwell, T. G. Mecca, J. Am. Chem. Soc. 1972, 94, 5829-5837.
24. [4b] T.-S. Chou, S.-J. Lee, M.-L. Peng, D.-J. Sun, S.-S. P. Chou, J. Org. Chem. 1988, 53, 3027-3031.
25. [4c] K. Banert, Chem. Ber. 1989, 122, 1963-1967.
26. [4d] C. Nájera, A. Pérez-Pinar, J. M. Sansano, Tetrahedron 1991, 47, 6337-6352.
27. [4e] E. Öhler, S. Kanzler, Liebigs Ann. Chem. 1994, 867-876.
28. [4f] R. V. Hoffmann, B. S. Severns, J. Org. Chem. 1996, 61, 5567-5573.
29. J. H. Bowie, B. Nussey, A. D. Ward, Aust. J. Chem. 1973, 26, 2547-2551.
30. [6a] A. L. Logothetis, J. Org. Chem. 1964, 29, 3049-3052.
31. [6b] V. Nair, J. Org. Chem. 1968, 33, 2121-2123, 4316.
32. [6c] T. C. Gallagher, R. C. Storr, Tetrahedron Lett. 1981, 22, 2909-2912.
33. F. W. Fowler, A. Hassner, L. A. Levy, J. Am. Chem. Soc. 1967, 89, 2077-2082.
34. A. Hassner, F. W. Fowler, J. Org. Chem. 1968, 33, 2686-2691.
35. J. E. Mulvaney, D. Savage, J. Org. Chem. 1971, 36, 2592-2596.
36. R. Maroni, G. Melloni, G. Modena, J. Chem. Soc., Perkin Trans. 1 1974, 353-356.
37. G. Boche, K. Buckl, D. Martens, D. R. Schneider, Liebigs Ann. Chem. 1980, 1135-1171.
38. R. E. Lutz, E. H. Rinker, Jr., J. Am. Chem. Soc. 1955, 77, 366-369.
39. F. Bergmann, J. Org. Chem. 1941, 6, 543-549.
40. H. O. House, D. J. Reif, J. Am. Chem. Soc. 1955, 77, 6525-6532.
41. M. Jayamani, N. Pant, S. Ananthan, K. Narayanan, C. N. Pillai, Tetrahedron 1986, 42, 4325-4332.
42. The reaction of 5 with bromine led to 12, which was first erroneously identified as 2,3-diphenyl-1H-indene: A. Orechoff, Ber. Dtsch. Chem. Ges. 1914, 47, 89-95; P. Ruggli, Justus Liebigs Ann. Chem. 1917, 414, 125-130. Analogous indenes were produced on treatment of 1,3,3-triphenylprop-1-enes with NBS. In these cases, no intermediate allylic bromides were detected: K. Yamamura, H. Miyake, A. Sera, Bull. Chem. Soc. Jpn. 1986, 59, 3699-3701.
43. The reaction of 5 with bromine led to 12, which was first erroneously identified as 2,3-diphenyl-1H-indene: A. Orechoff, Ber. Dtsch. Chem. Ges. 1914, 47, 89-95; P. Ruggli, Justus Liebigs Ann. Chem. 1917, 414, 125-130. Analogous indenes were produced on treatment of 1,3,3-triphenylprop-1-enes with NBS. In these cases, no intermediate allylic bromides were detected: K. Yamamura, H. Miyake, A. Sera, Bull. Chem. Soc. Jpn. 1986, 59, 3699-3701.
44. The reaction of 5 with bromine led to 12, which was first erroneously identified as 2,3-diphenyl-1H-indene: A. Orechoff, Ber. Dtsch. Chem. Ges. 1914, 47, 89-95; P. Ruggli, Justus Liebigs Ann. Chem. 1917, 414, 125-130. Analogous indenes were produced on treatment of 1,3,3-triphenylprop-1-enes with NBS. In these cases, no intermediate allylic bromides were detected: K. Yamamura, H. Miyake, A. Sera, Bull. Chem. Soc. Jpn. 1986, 59, 3699-3701.
45. Analogous procedure: A. L. Logothetis, J. Am. Chem. Soc. 1965, 87, 749-754.
46. H. Staudinger, A. Gaule, Ber. Dtsch. Chem. Ges. 1916, 49, 1897-1918.
47. The erroneous structural analysis[5] has been "borrowed" in the literature: [19a] D. J. Anderson, A. Hassner, Synthesis 1975, 483-495.
48. [19b] V. Nair in The Chemistry of Heterocyclic Compounds, Small-Ring Heterocycles, Vol. 42, Part 1 (Ed.: A. Hassner), Wiley, New York, 1983, pp. 215-332.
49. [19c] J. H. Bowie, B. Nussey, J. Chem. Soc., Perkin Trans. 1 1973, 1693-1696.
50. [19d] J. Backes in Houben-Weyl, Vol. E 16c (Ed.: D. Klamann), Thieme, Stuttgart, 1992, p. 365.
51. A. Klages, S. Heilmann, Ber. Dtsch. Chem. Ges. 1904, 37, 1447-1457.
52. This method of dehydration was introduced by G. G. Hazen, D. W. Rosenburg, J. Org. Chem. 1964, 29, 1930-1932.
53. S. Miyano, Y. Sako, Chem. Pharm. Bull. 1965, 13, 1372-1373.
54. Analogous procedures: P. A. S. Smith, E. E. Most, Jr., J. Org. Chem. 1957, 22, 358-362.
55. A. Gagneux, S. Winstein, W. G. Young, J. Am. Chem. Soc. 1960, 82, 5956-5957.
56. K. Banert, Chem. Ber. 1985, 118, 1564-1574.
57. [26a] R. J. Sundberg, B. C. Pearce, J. Org. Chem. 1982, 47, 725-730.
58. [26b] A. Saito, K. Saito, A. Tanaka, T. Oritani, Tetrahedron Lett. 1997, 38, 3955-3958.
59. L. F. Hatch, H. E. Alexander, J. Am. Chem. Soc. 1950, 72, 5643-5645.
60. The analogous photochemical cis - trans equilibration of (E)-21a and (Z)-21a: E. K. Raunio, W. A. Bonner, J. Org. Chem. 1966, 31, 396-399.
61. Alternative synthesis of (E)-21c: [29a] S.-I. Murahashi, Y. Taniguchi, Y. Imada, Y. Tanigawa, J. Org. Chem. 1989, 54, 3292-3303.
62. [29b] Y. Uozumi, H. Danjo, T. Hayashi, Tetrahedron Lett. 1997, 38, 3557-3560.
63. R. Lespieau, R. L. Wakeman, Bull. Soc. Chim. Fr. 1932, 51, 384-400.
64. [31a] M. Hamada, T. Suzuki, Botyu Kagaku 1954, 19, 76-80 [Chem. Abstr. 1955, 49, 9520e].
65. [31a] M. Hamada, T. Suzuki, Botyu Kagaku 1954, 19, 76-80 [Chem. Abstr. 1955, 49, 9520e].
66. [31b] R. T. LaLonde, P. B. Ferrara, A. D. Debboli, Jr., J. Org. Chem. 1972, 37, 1094-1099.
67. [32a] L. D. Sychkova, O. L. Kalinkina, Y. S. Shabarov, Zh. Org. Khim. 1981, 17, 1435-1440; J. Org. Chem. USSR 1981, 17, 1277-1281.
68. [32a] L. D. Sychkova, O. L. Kalinkina, Y. S. Shabarov, Zh. Org. Khim. 1981, 17, 1435-1440; J. Org. Chem. USSR 1981, 17, 1277-1281.
69. [32b] L. Capuano, A. Willmes, Liebigs Ann. Chem. 1982, 80-86.
70. [33a] A. Alberola, M. S. Esteban, F. J. Lopez, An. Quim. 1978, 74, 761-765.
71. [33b] M. M. Bokadia, B. R. Brown, D. Cobern, A. Roberts, G. A. Somerfield, J. Chem. Soc. 1962, 1658-1666.
72. J. B. Woell, P. Boudjouk, J. Org. Chem. 1980, 45, 5213 and references cited therein.
73. The isomerization 24b → 25 was postulated to be involved in the transformation of indene into 25 by treatment with iodine azide and subsequent elimination of hydrogen iodide, see ref. [8]
74. G. Jones, P. M. Radley, J. Chem. Soc., Perkin Trans, 1 1982, 1123-1130.
75. [37a] H. Stobbe, K. Niedenzu, Ber. Dtsch. Chem. Ges. 1901, 34, 3897-3913.
76. [37b] W. B. Black, R. E. Lutz, J. Am. Chem. Soc. 1953, 75, 5990-5997.
77. Treatment of 3-azido-1, 1,2-triphenylpropene with potassium t-butoxide led to an analogous reaction: A. Hassner, J. S. Teeter, J. Org. Chem. 1970, 35, 3397-3401.
78. R. E. Lutz, J. O. Weiss, J. Am. Chem. Soc. 1955, 77, 1814-1818.
79. [40a] J. F. Normant, H. Deshayes, Bull. Soc. Chim. Fr. 1972, 2854-2859.
80. [40b] J. Hubert, T. Theophanides, J. Organomet. Chem. 1975, 93, 265-280.
81. [40c] H. Shima, N. Furukawa, Tetrahedron 1995, 51, 12239-12256.
82. [40d] E. C. Friedrich, C. B. Abma, J. Am. Chem. Soc. 1980, 102, 1367-1371.
83. [41a] S. G. Alvarez, M. T. Alvarez, Synthesis 1997, 413-414.
84. [41b] R. R. Fraser, Gurudata, R. N. Renaud, C. Reyes-Zamora, R. B. Swingle, Can. J. Chem. 1969, 47, 2767-2773.
85. [42a] G. Cainelli, M. Contento, F. Manescalchi, L. Plessi, M. Panunzio, Synthesis 1983, 306-308.
86. [42b] T. Hudlicky, H. F. Olivo, M. G. Natchus, E. F. Umpierrez, E. Pandolfi, C. Volonterio, J. Org. Chem. 1990, 55, 4767-4770.
87. [43a] M. P. Ponomarchuk, L. S. Sologub, L. F. Kasukhin, V. P. Kukhar', Zh. Obshch. Khim. 1985, 55, 1725-1730; J. Gen. Chem. USSR (Engl. Transl.) 1985, 55, 1532-1536.
88. [43a] M. P. Ponomarchuk, L. S. Sologub, L. F. Kasukhin, V. P. Kukhar', Zh. Obshch. Khim. 1985, 55, 1725-1730; J. Gen. Chem. USSR (Engl. Transl.) 1985, 55, 1532-1536.
89. [43b] E. Pretsch, T. Clerc, J. Seibl, W. Simon, Tabellen zur Strukturaufklärung organischer Verbindungen mit spektroskopischen Methoden, 3rd. ed., Springer, Berlin, 1990.
90. [44a] D. D. Tanner, Y. Kosugi, R. Arhart, N. Wada, T. Pace, T. Ruo, J. Am. Chem. Soc. 1976, 98, 6275-6284.
91. [44b] E. D. Matveeva, A. S. Erin, D. B. Mitroshin, A. L. Kurts, Zh. Org. Khim. 1995, 31, 1121-1125; Russ. J. Org. Chem. 1995, 31, 1019-1022.
92. [44b] E. D. Matveeva, A. S. Erin, D. B. Mitroshin, A. L. Kurts, Zh. Org. Khim. 1995, 31, 1121-1125; Russ. J. Org. Chem. 1995, 31, 1019-1022.
93. L. J. Stangeland, J. Songstad, Acta Chem. Scand. 1970, 24, 356-358.
94. R. M. Parkhurst, J. O. Rodin, R. M. Silverstein, J. Org. Chem. 1963, 28, 120-123.
95. D. E. Bergstrom, M. W. Ng, J. J. Wong, J. Org. Chem. 1983, 48, 1902-1903.
96. R. Maroni, G. Melloni, G. Modena, J. Chem. Soc., Perkin Trans. 1 1973, 2491-2496.
97. F. Marcuzzi, G. Melloni, Gazz. Chim. Ital. 1975, 105, 495-507.
98. L. M. Tolbert, M. Z. Ali, J. Org. Chem. 1985. 50, 3288-3295.
99. N. F. Woolsey, L. J. Radonovich, F. M. Saad, M. Brostrom, J. Org. Chem. 1984, 49, 1937-1941.
100. R. S. Hansen, W. S. Trahanovsky, J. Org. Chem. 1974, 39, 570-571.
101. L. F. Tietze, T. Eicher, Reaktionen und Synthesen im organischchemischen Praktikum und Forschungslaboratorium. Thieme, Stuttgart, 1991, p. 40.
102. C. Berti, L. Greci, M. Poloni, J. Chem. Soc., Perkin Trans. 1 1981, 1610-1613.