Access to the naphthylcarbene rearrangement manifold via isomeric benzodiazocycloheptatrienes

Journal of Organic Chemistry

Volumn 67, Issue 25, 2002, Pages 9031-9042

  Bonvallet, Paul A ^a   Todd, Eric M ^a   Kim, Yong Seol ^a   McMahon, Robert J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOPRODUCTS;

ARGON; INFRARED SPECTROSCOPY; IRRADIATION; PHOTOLYSIS; ULTRAVIOLET SPECTROSCOPY;

AROMATIC COMPOUNDS;

ALLENE DERIVATIVE; AZO COMPOUND; BENZENE DERIVATIVE; CARBENOID; NAPHTHYL GROUP;

ARTICLE; ELECTRON SPIN RESONANCE; INFRARED SPECTROSCOPY; IRRADIATION; ISOMER; PHOTOLYSIS; RING OPENING; ULTRAVIOLET SPECTROSCOPY;

EID: 0037073886     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020304z     Document Type: Article

References (68)

1. For reviews and leading references on carbenes, see: (a) Tomioka, H. Bull. Chem. Soc. Jpn. 1998, 71, 1501-1524. (b) Platz, M. S.; Modarelli, D. A.; Morgan, S.; White, W. R.; Mullins, M.; Çelebi, S.; Toscano, J. P. Prog. React. Kinet. 1994, 19, 93-137. (c) Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 1993, 93, 1583-1671. (d) Platz, M. S. Kinetics and Spectroscopy of Carbenes and Biradicals; Plenum: New York, 1990. (e) Kirmse, W. Carbene Chemistry, 2nd Ed.; Academic Press: New York, 1971. (f) Zeller, K.-P.; Gugel, H. In Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme: Stuttgart, 1989; Vol. E19b, pp 165-336.
2. For reviews and leading references on carbenes, see: (a) Tomioka, H. Bull. Chem. Soc. Jpn. 1998, 71, 1501-1524. (b) Platz, M. S.; Modarelli, D. A.; Morgan, S.; White, W. R.; Mullins, M.; Çelebi, S.; Toscano, J. P. Prog. React. Kinet. 1994, 19, 93-137. (c) Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 1993, 93, 1583-1671. (d) Platz, M. S. Kinetics and Spectroscopy of Carbenes and Biradicals; Plenum: New York, 1990. (e) Kirmse, W. Carbene Chemistry, 2nd Ed.; Academic Press: New York, 1971. (f) Zeller, K.-P.; Gugel, H. In Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme: Stuttgart, 1989; Vol. E19b, pp 165-336.
3. For reviews and leading references on carbenes, see: (a) Tomioka, H. Bull. Chem. Soc. Jpn. 1998, 71, 1501-1524. (b) Platz, M. S.; Modarelli, D. A.; Morgan, S.; White, W. R.; Mullins, M.; Çelebi, S.; Toscano, J. P. Prog. React. Kinet. 1994, 19, 93-137. (c) Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 1993, 93, 1583-1671. (d) Platz, M. S. Kinetics and Spectroscopy of Carbenes and Biradicals; Plenum: New York, 1990. (e) Kirmse, W. Carbene Chemistry, 2nd Ed.; Academic Press: New York, 1971. (f) Zeller, K.-P.; Gugel, H. In Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme: Stuttgart, 1989; Vol. E19b, pp 165-336.
4. For reviews and leading references on carbenes, see: (a) Tomioka, H. Bull. Chem. Soc. Jpn. 1998, 71, 1501-1524. (b) Platz, M. S.; Modarelli, D. A.; Morgan, S.; White, W. R.; Mullins, M.; Çelebi, S.; Toscano, J. P. Prog. React. Kinet. 1994, 19, 93-137. (c) Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 1993, 93, 1583-1671. (d) Platz, M. S. Kinetics and Spectroscopy of Carbenes and Biradicals; Plenum: New York, 1990. (e) Kirmse, W. Carbene Chemistry, 2nd Ed.; Academic Press: New York, 1971. (f) Zeller, K.-P.; Gugel, H. In Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme: Stuttgart, 1989; Vol. E19b, pp 165-336.
5. For reviews and leading references on carbenes, see: (a) Tomioka, H. Bull. Chem. Soc. Jpn. 1998, 71, 1501-1524. (b) Platz, M. S.; Modarelli, D. A.; Morgan, S.; White, W. R.; Mullins, M.; Çelebi, S.; Toscano, J. P. Prog. React. Kinet. 1994, 19, 93-137. (c) Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 1993, 93, 1583-1671. (d) Platz, M. S. Kinetics and Spectroscopy of Carbenes and Biradicals; Plenum: New York, 1990. (e) Kirmse, W. Carbene Chemistry, 2nd Ed.; Academic Press: New York, 1971. (f) Zeller, K.-P.; Gugel, H. In Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme: Stuttgart, 1989; Vol. E19b, pp 165-336.
6. For reviews and leading references on carbenes, see: (a) Tomioka, H. Bull. Chem. Soc. Jpn. 1998, 71, 1501-1524. (b) Platz, M. S.; Modarelli, D. A.; Morgan, S.; White, W. R.; Mullins, M.; Çelebi, S.; Toscano, J. P. Prog. React. Kinet. 1994, 19, 93-137. (c) Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 1993, 93, 1583-1671. (d) Platz, M. S. Kinetics and Spectroscopy of Carbenes and Biradicals; Plenum: New York, 1990. (e) Kirmse, W. Carbene Chemistry, 2nd Ed.; Academic Press: New York, 1971. (f) Zeller, K.-P.; Gugel, H. In Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme: Stuttgart, 1989; Vol. E19b, pp 165-336.
7. Jones, W. M. Angew. Chem., Int. Ed. Engl 1972, 11, 325-326.
8. Mitsuhashi, T.; Jones, W. M. J. Am. Chem. Soc. 1972, 94, 677-679.
9. Krajca, K. E.; Mitsuhashi, T.; Jones, W. M. J. Am. Chem. Soc. 1972, 94, 3661-3662.
10. Jones, W. M.; Joines, R. C.; Myers, J. A.; Mitsuhashi, T.; Krajca, K. E.; Waali, E. E.; Davis, T. L.; Turner, A. B. J. Am. Chem. Soc. 1973, 95, 826-835.
11. Tyner, R. L.; Jones, W. M.; Ohm, Y.; Sabin, J. R. J. Am. Chem. Soc. 1974, 96, 3765-3769.
12. Coburn, T. T.; Jones, W. M. J. Am. Chem. Soc. 1974, 96, 5218-5227.
13. Jones, W. M. Acc. Chem. Res. 1977,10, 353-359.
14. Waali, E. E.; Lewis, J. M.; Lee, D. E.; Allen, E. W. I.; Chappell, A. K. J. Org. Chem. 1977, 42, 3460-3462.
15. Becker, J.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1980, 190-191.
16. West, P. R.; Mooring, A. M.; McMahon, R. J.; Chapman, O. L. J. Org. Chem. 1986, 51, 1316-1320.
17. Chateauneuf, J. E.; Horn, K. A.; Savino, T. G. J. Am. Chem. Soc. 1988, 110, 539-545.
18. Albrecht, S. W.; McMahon, R. J. J. Am. Chem. Soc. 1993, 115, 855-859.
19. Xie, Y.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F. J. Am. Chem. Soc. 1997, 119, 1370-1377.
20. Bonvallet, P. A.; McMahon, R. J. J. Am. Chem. Soc. 1999, 121, 10496-10503.
21. Bonvallet, P. A.; McMahon, R. J. J. Am. Chem. Soc. 2000, 122, 9332-9333.
22. Zheng, F.; McKee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1999, 121, 11237-11238.
23. Kaiser, R. I.; Asvany, O.; Lee, Y. T. Planet. Space Sci. 2000, 48, 483-492.
24. (a) West, P. R.; Chapman, O. L.; LeRoux, J.-P. J. Am. Chem. Soc. 1982, 104, 1779-1782.
25. (b) McMahon, R. J.; Abelt, C. J.; Chapman, O. L.; Johnson, J. W.; Kreil, C. L.; LeRoux, J.-P.; Mooring, A. M.; West, P. R. J. Am. Chem. Soc. 1987,109, 2456-2459.
26. (c) Matzinger, S.; Bally, T. J. Phys. Chem. A 2000, 104, 3544-3552.
27. Matzinger, S.; Bally, T. J. Phys. Chem. A 2000, 104, 3544- 3552.
28. Radom, L.; Schaefer, H. F.; Vincent, M. A. Nouv. J. Chim. 1980, 4, 411-415.
29. Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535-1542.
30. Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 61, 7022-7029.
31. Schreiner, P. R.; Karney, W. L.; Schleyer, P. v. R.; Borden, W. T.; Hamilton, T. P.; Schaefer, H. F. J. Org. Chem. 1996, 61, 7030-7039.
32. Kuzaj, M.; Lüerssen, H.; Wentrup, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 480-482.
33. McMahon, R. J.; Chapman, O. L. J. Am. Chem. Soc. 1986, 108, 1713-1714.
34. Evans, R. A.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 4009-4017, footnote 26.
35. Balci, M.; Winchester, W. R.; Jones, W. M. J. Org. Chem. 1982, 47, 5180-5186.
36. Reference 8, footnote 19.
37. Kirmse, W.; Loosen, K.; Sluma, H.-D. J. Am. Chem. Soc. 1981, 103, 5935-5937.
38. Kirmse, W.; Sluma, H.-D. J. Org. Chem. 1988, 53, 763-767.
39. (a) Chemistry of Diazirines; Liu, M. H. T., Ed.; CRC Press: Boca Raton, FL, 1987.
40. (b) Schmitz, E. Adv. Heterocycl. Chem. 1979, 24, 63-107.
41. (a) Skancke, A.; Hosmane, R. S.; Liebman, J. F. Acta Chem. Scand. 1998, 52, 967-974.
42. (b) Jug, K. J. Org. Chem. 1983, 48, 1344-1348.
43. (c) Nozoe, T.; Mukai, T.; Takase, K. Chem. Abstr. 1957, 51, 7316.
44. Information available as Supporting Information.
45. Nakagawa, K.; Konaka, R.; Nakata, T. J. Org. Chem. 1962, 27, 1597-1601.
46. West, P. R. Ph.D. Dissertation, University of California, Los Angeles, 1981.
47. Trozzolo, A. M.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1965, 87, 129-130.
48. Wasserman, E.; Snyder, L. C.; Yager, W. A. J. Chem. Phys. 1964, 41, 1763-1772.
49. -1.
50. Carrington, A.; McLachlan, A. D. Introduction to Magnetic Resonance; Harper & Row: New York, 1967.
51. Moritani, I.; Murahashi, S.-I.; Nishino, M.; Yamamoto, Y.; Itoh, K.; Mataga, N. J. Am. Chem. Soc. 1967, 89, 1259-1260.
52. Qualitatively identical results are obtained when 16 is prepared from the low-temperature oxidation of 24, although the material is less pure and present in smaller amounts.
53. Senthilnathan, V. P.; Platz, M. S. J. Am. Chem. Soc. 1981, 103, 5503-5511.
54. Roth, H. D.; Hutton, R. S. Tetrahedron 1985, 41, 1567-1578.
55. Kuzaj, M. Ph.D. Thesis, University of Marburg, Germany, 1985.
56. Lüerssen, H. Ph.D. Thesis, University of Marburg, 1985.
57. This species is also reported in the Supporting Information of ref 16.
58. Kuhn, A.; Vosswinkel, M.; Wentrup, C. J. Org. Chem. 2002, 67, 9023-9030.
59. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO 4.0; Theoretical Chemistry Institute, University of Wisconsin: Madison, 1996.
60. For a recent review and leading references, see: Platz, M. S. In Advances in Carbene Chemistry II; Brinker, U., Ed.; JAI Press: Boca Raton, FL, 1998; Vol. 2, p 133.
61. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
62. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B-Condens Matter 1988, 37, 785-789.
63. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
64. McMahon, R. J.; Chapman, O. L.; Hayes, R. A.; Hess, T. C.; Krimmer, H.-P. J. Am. Chem. Soc. 1985, 107, 7597-7606.
65. Seburg, R. A.; McMahon, R. J. J. Am. Chem. Soc. 1992, 114, 7183-7189.
66. Rona, P. J. Chem. Soc. 1962, 3629-3635.
67. Srivastava, K. C.; Dev, S. Tetrahedron 1972, 28, 1083-1091.
68. Broadus, K. M.; Kass, S. R. J. Org. Chem. 2000, 65, 6566-6571.