Thermal migration of an ethynyl group from one benzene ring to another by reversible vinylidene C-H insertion

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1877-1880

  Scott, Lawrence T ^a   Necula, Atena ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BENZENE; FUNCTIONAL GROUP;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; STEREOISOMERISM; TEMPERATURE;

EID: 0031575742     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00225-6     Document Type: Article

References (27)

1. (1) Presented at the Northeast Regional Meeting of the American Chemical Society, Burlington, VT, June, 1994 and at the Eighth International Symposium on Novel Aromatic Compounds, Braunschweig, Germany, August, 1995.
2. (1) Presented at the Northeast Regional Meeting of the American Chemical Society, Burlington, VT, June, 1994 and at the Eighth International Symposium on Novel Aromatic Compounds, Braunschweig, Germany, August, 1995.
3. (2) Brown, R. F. C.; Eastwood, F. W.; Jackman, G. P. Aust. J. Chem. 1977, 30, 1757-67.
4. f (AM1;PM3): 1 (158.0; 140.2), 7 (141.1; 124.2), 8 (133.0; 116.6), 13 (158.2; 145.4), and 14 (159.1; 146.3).
5. (4) The only prior example of a carbene extrusion from a remote (non-adjacent) C-H bond that we know of is the one reported by Adeney, M.; Brown, R. F. C.; Coulston, K. J.; Eastwood, F. W.; James, I. W. Aust. J. Chem. 1991, 44, 967-80; Brown, R. F. C.; Eastwood, F. W.; Wong, N. R. Tetrahedron Lett. 1993, 34, 1223-6.
6. (4) The only prior example of a carbene extrusion from a remote (non-adjacent) C-H bond that we know of is the one reported by Adeney, M.; Brown, R. F. C.; Coulston, K. J.; Eastwood, F. W.; James, I. W. Aust. J. Chem. 1991, 44, 967-80; Brown, R. F. C.; Eastwood, F. W.; Wong, N. R. Tetrahedron Lett. 1993, 34, 1223-6.
7. (5) Stone, A. J.; Wales, D. J. Chem. Phys. Lett. 1986, 128, 501-3; Murry, R. L.; Strout, D. L.; Odom, G. K.; Scuseria, G. E. Nature 1993, 366, 665-7; Hawkins, J. M.; Nambu, M.; Meyer, A. J. Am. Chem. Soc. 1994, 116, 7642-5 and references cited therein.
8. (5) Stone, A. J.; Wales, D. J. Chem. Phys. Lett. 1986, 128, 501-3; Murry, R. L.; Strout, D. L.; Odom, G. K.; Scuseria, G. E. Nature 1993, 366, 665-7; Hawkins, J. M.; Nambu, M.; Meyer, A. J. Am. Chem. Soc. 1994, 116, 7642-5 and references cited therein.
9. (5) Stone, A. J.; Wales, D. J. Chem. Phys. Lett. 1986, 128, 501-3; Murry, R. L.; Strout, D. L.; Odom, G. K.; Scuseria, G. E. Nature 1993, 366, 665-7; Hawkins, J. M.; Nambu, M.; Meyer, A. J. Am. Chem. Soc. 1994, 116, 7642-5 and references cited therein.
10. (6) Compounds 4 and 6 were first reported by Kobayashi, E.; Jiang, J.; Furukawa, J. Polym. J. 1990, 22, 266-73; Kobayashi, E.; Jiang, J.; Ohta, H.; Furukawa, J. J. Polym. Sci., A: Polym. Chem. 1990, 28, 2641-50.
11. (6) Compounds 4 and 6 were first reported by Kobayashi, E.; Jiang, J.; Furukawa, J. Polym. J. 1990, 22, 266-73; Kobayashi, E.; Jiang, J.; Ohta, H.; Furukawa, J. J. Polym. Sci., A: Polym. Chem. 1990, 28, 2641-50.
12. 13C NMR, and high resolution mass spectroscopy.
13. (8) Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4.
14. (9) Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992; Cheng, P.-C., M.S. thesis, University of Nevada, Reno, 1992; Scott, L. T. Pure Appl. Chem. 1996, 68, 291-300 and references cited therein. See also Jenneskens, L. W.; Sarobe, M.; Zwikker, J. W. Pure Appl. Chem. 1996, 68, 219-24.
15. (9) Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992; Cheng, P.-C., M.S. thesis, University of Nevada, Reno, 1992; Scott, L. T. Pure Appl. Chem. 1996, 68, 291-300 and references cited therein. See also Jenneskens, L. W.; Sarobe, M.; Zwikker, J. W. Pure Appl. Chem. 1996, 68, 219-24.
16. (9) Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992; Cheng, P.-C., M.S. thesis, University of Nevada, Reno, 1992; Scott, L. T. Pure Appl. Chem. 1996, 68, 291-300 and references cited therein. See also Jenneskens, L. W.; Sarobe, M.; Zwikker, J. W. Pure Appl. Chem. 1996, 68, 219-24.
17. (9) Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992; Cheng, P.-C., M.S. thesis, University of Nevada, Reno, 1992; Scott, L. T. Pure Appl. Chem. 1996, 68, 291-300 and references cited therein. See also Jenneskens, L. W.; Sarobe, M.; Zwikker, J. W. Pure Appl. Chem. 1996, 68, 219-24.
18. (10) Formation of 7 by FVP of 9 and isomerization of 7 to 8 were discovered independently by Sarobe, M.; Snoeijer, J. D.; Jenneskens, L. W.; Zwikker, J. W.; Wesseling, J. Tetrahedron Lett. 1995, 36, 9565-6.
19. 2 carrier gas leak, net pressure 1 torr.
20. (12) Scott, L. T.; Roelofs, N. H. J. Am. Chem. Soc. 1987, 109, 5461-5; Scott, L. T.; Roelofs, N. H. Tetrahedron Lett. 1988, 29, 6857-60; Scott, L. T.; Hashemi, M. M.; Schultz, T. H.; Wallace, M. B. J. Am. Chem. Soc. 1991,113, 9692-3.
21. (12) Scott, L. T.; Roelofs, N. H. J. Am. Chem. Soc. 1987, 109, 5461-5; Scott, L. T.; Roelofs, N. H. Tetrahedron Lett. 1988, 29, 6857-60; Scott, L. T.; Hashemi, M. M.; Schultz, T. H.; Wallace, M. B. J. Am. Chem. Soc. 1991,113, 9692-3.
22. (12) Scott, L. T.; Roelofs, N. H. J. Am. Chem. Soc. 1987, 109, 5461-5; Scott, L. T.; Roelofs, N. H. Tetrahedron Lett. 1988, 29, 6857-60; Scott, L. T.; Hashemi, M. M.; Schultz, T. H.; Wallace, M. B. J. Am. Chem. Soc. 1991,113, 9692-3.
23. 7
24. (b) House, H. O.; Ghali, N. I.; Haack, J. L.; VanDerveer, D. J. Org. Chem. 1980, 45, 1807-17.
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27. 3): δ 8.73 (s, 1H), 8.22 (d, 1H, J = 8.6 Hz), 8.12 (d, 1H, J = 8.8 Hz), 7.79 (d, 1H, J = 6.7 Hz), 7.72 (d, 1H, J = 6.8 Hz), 7.60 (d, 1H, J = 5.1 Hz), 7.59 (t, 1H, J = 7.3 Hz), 7.47 (t, 1H, J = 7.2 Hz), 7.06 (d, 1H, J = 5.4 Hz), 3.61 (s, 1H).