2-Biphenylenylcarbene

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5368-5371

  Wu, Guoxian ^a   Jones Jr , Maitland ^a   Walton, Richard ^b   Lahti, Paul M ^b  

^a PRINCETON UNIVERSITY   (United States)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005761836     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980169j     Document Type: Article

References (30)

1. We thank the National Science Foundation for support of this work at Princeton through Grants NSF CHE-9322579 and CHE-9702823 and at Massachusetts through CHE-9521594.
2. For a summary of arylcarbene chemistry, see: Wentrup, C. In Methoden der Organische Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme Verlag: Stuttgart, 1989; Vol. E19b, pp 824-976.
3. Platz, M. S.; Maloney, V. M. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990; Chapter 8.
4. For an overview, see ref 3; for particular typical and thorough studies see: (a) Barcus, R. L.; Hadel, L. M.; Johnston, L. J.; Platz, M. S.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1986, 108, 3928 (1-naphthylcarbene). ( b) Horn, K. A.; Chateauneuf, J. E. Tetrahedron 1985, 41, 1465 (2-naphthylcarbene).
5. For an overview, see ref 3; for particular typical and thorough studies see: (a) Barcus, R. L.; Hadel, L. M.; Johnston, L. J.; Platz, M. S.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1986, 108, 3928 (1-naphthylcarbene). ( b) Horn, K. A.; Chateauneuf, J. E. Tetrahedron 1985, 41, 1465 (2-naphthylcarbene).
6. For early product studies see: Jones, M., Jr.; Rettig, K. R. J. Am. Chem. Soc. 1965, 87, 4013. Jones, M., Jr.; Rettig, K. R. J. Am. Chem. Soc. 1965, 87, 4015. For more recent spectroscopic work, see: Griller, D.; Hadel, L.; Nazran, A. S.; Platz, M. S.; Wong, P. C.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 2227.
7. For early product studies see: Jones, M., Jr.; Rettig, K. R. J. Am. Chem. Soc. 1965, 87, 4013. Jones, M., Jr.; Rettig, K. R. J. Am. Chem. Soc. 1965, 87, 4015. For more recent spectroscopic work, see: Griller, D.; Hadel, L.; Nazran, A. S.; Platz, M. S.; Wong, P. C.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 2227.
8. For early product studies see: Jones, M., Jr.; Rettig, K. R. J. Am. Chem. Soc. 1965, 87, 4013. Jones, M., Jr.; Rettig, K. R. J. Am. Chem. Soc. 1965, 87, 4015. For more recent spectroscopic work, see: Griller, D.; Hadel, L.; Nazran, A. S.; Platz, M. S.; Wong, P. C.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 2227.
9. Product studies: Baron, W. J.; Hendrick, M. E.; Jones, M., Jr. J. Am. Chem. Soc. 1973, 95, 6286. Spectroscopic work: Eisenthal, K. B.; Turro, N. J.; Sitzman, E. V.; Gould, I. R.; Hefferon, J.; Lamgan, J.; Cha, Y. Tetrahedron, 1985, 41, 1543.
10. Product studies: Baron, W. J.; Hendrick, M. E.; Jones, M., Jr. J. Am. Chem. Soc. 1973, 95, 6286. Spectroscopic work: Eisenthal, K. B.; Turro, N. J.; Sitzman, E. V.; Gould, I. R.; Hefferon, J.; Lamgan, J.; Cha, Y. Tetrahedron, 1985, 41, 1543.
11. Garratt, P. J. Aromaticity; Wiley: New York, 1986; p 234ff.
12. Buckland, P. R.; McOmie, J. F. W. Tetrahedron 1977, 33, 1797.
13. Closs, G. L.; Moss, R. A. J. Am. Chem. Soc. 1964, 86, 4042. Gutsche, C. D.; Bachman, G. L.; Coffey, R. S. Tetrahedron 1962, 18, 617.
14. Closs, G. L.; Moss, R. A. J. Am. Chem. Soc. 1964, 86, 4042. Gutsche, C. D.; Bachman, G. L.; Coffey, R. S. Tetrahedron 1962, 18, 617.
15. Chari, S. L.; Chiang, S.-H.; Jones, M., Jr. J. Am. Chem. Soc. 1982, 104, 3138.
16. A similar conclusion can be reached from a preliminary examination of the chemistry and spectroscopy of the 1-substituted biphenylenylcarbene. This system is harder to investigate than 1, because starting materials are less stable, the syntheses are less efficient, and the separations of products are more difficult.
17. Trozzolo, A, M. Acc. Chem. Res. 1968, 1, 329.
18. Brandon, R. W.; Closs, G. L.; Hutchison, C. A. J. Chem. Phys. 1962, 37, 1878, Murray, R. W.; Trozzolo, A. M.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1962, 84, 3213, Hutchison, C. A.; Kohler, B. E. J. Chem. Phys. 1969, 51, 3327.
19. Brandon, R. W.; Closs, G. L.; Hutchison, C. A. J. Chem. Phys. 1962, 37, 1878, Murray, R. W.; Trozzolo, A. M.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1962, 84, 3213, Hutchison, C. A.; Kohler, B. E. J. Chem. Phys. 1969, 51, 3327.
20. Brandon, R. W.; Closs, G. L.; Hutchison, C. A. J. Chem. Phys. 1962, 37, 1878, Murray, R. W.; Trozzolo, A. M.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1962, 84, 3213, Hutchison, C. A.; Kohler, B. E. J. Chem. Phys. 1969, 51, 3327.
21. Trozzolo, A. M.; Murray, R. W.; Wasserman, E. J. Am. Chem. Soc. 1962, 84, 4990.
22. Trozzolo, A. M.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1965, 87, 129.
23. During the melting point determination bubbles evolved and the azine was formed.
24. Miller, J. B. J. Org. Chem. 1959, 24 560.
25. (a) Belford, G. G.; Belford, R. L.; Burkhalter, J. F. J. Magn. Reson. 1973, 11, 251.
26. (b) Teki, Y.; Takui, T.; Yagi, H.; Itoh, K.; Iwamura, H. J. Chem. Phys. 1985, 83, 539.
27. (c) Teki, Y.; Takui, T.; Itoh, K. J. Chem. Phys. 1988, 88, 6134.
28. (d) Teki, Y.; Fujita, I.; Takui, T.; Kinoshita, T.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 11499.
29. (e) Teki, Y., Ph.D. Thesis, Osaka City University, Osaka, Japan, 1985.
30. (f) Details of the line shape program used by us are described in Sato, K. Ph.D. Thesis, Osaka City University, Osaka, Japan, 1994. We thank Prof. Sato for allowing us the use of this program.