Generation and characterization of triplet anthryl(aryl)carbenes

Organic Letters

Volumn 2, Issue 19, 2000, Pages 2995-2997

  Itakura, Hidetaka ^a   Tomioka, Hideo ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011262167     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006308c     Document Type: Article

References (19)

1. Wasserman, E.; Kuck, V. J.; Yager, W. A.; Hutton, R. S.; Greene, F. D.; Abegg, V. P.; Weinshenker, N. M. J. Am. Chem. Soc. 1971, 93, 6335.
2. Astles, D. J.; Girard, M.; Griller, D.; Kolt, J.; Wayner, D. D. J. Org. Chem. 1988, 53, 6053.
3. For review of carbenes, see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971.
4. (b) Regitz, M.; Ed. Carbene-(oide), Carbine; Houben-Weyl, Thieme: Stuttgart, 1989; Vol. E196.
5. (c) Moss, R. A., Jones, M., Jr., Eds. Carbenes; Wiley: New York, 1973, 1975; Vols. I and II.
6. See for reviews of persistent triplet carbenes: (a) Tomioka, H. Acc. Chem. Res. 1997, 30, 1315.
7. (b) Tomioka, H. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 2, pp 175-214.
8. -1.
9. See for reviews of the ESR spectra of triplet carbenes: (a) Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 1993, 93, 1583.
10. (b) Trozzolo, A. M.; Wasserman. E. In Carbenes; Jones, M., Jr., Moss, R. A.; Eds.; Wiley: New York, 1975; Vol. 2, pp 185-206.
11. (c) Tomioka, H. In Advances in Strained and Interesting Organic Molecules; Halton, B.; Ed.; JAI Press: Greenwich, CT, 2000; Vol. 8, pp 83-112.
12. A large number of triplet carbenes have been characterized by ESR spectroscopy since the pioneering work of Wasserman et al. Wasserman, E.; Snyder, L. C.; Yager, W. A.; J. Chem. Phys. 1964, 41, 1763. Wasserman, E.; Hutton, R. S. Acc. Chem. Res. 1977, 10, 27.
13. A large number of triplet carbenes have been characterized by ESR spectroscopy since the pioneering work of Wasserman et al. Wasserman, E.; Snyder, L. C.; Yager, W. A.; J. Chem. Phys. 1964, 41, 1763. Wasserman, E.; Hutton, R. S. Acc. Chem. Res. 1977, 10, 27.
14. Wasserman, E.; Trozzolo, A. M.; Yager, W. A. J. Chem. Phys. 1964, 40, 2408.
15. Trozzolo, A. M.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1965, 87, 129.
16. Itakura, H. Unpublished observation.
17. Fujiwara, Y.; Sasaki, M.; Tanimoto, Y.; Itoh, M. Chem. Phys. Lett. 1988, 146, 133.
18. Tukada, H.; Sugawara, T.; Murata, S.; Iwamura, H. Tetrahedron Lett. 1986. 27, 235.
19. The sample temperature was raised in 10 K increments to the desired temperature, allowed to stand there for 1 min, and then recooled to 77 K to measure the signal.