A triplet carbene that can almost be bottled [2]

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 10213-10214

  Hirai, Katsuyuki ^a   Tomioka, Hideo ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZENE; CARBON; FLUORINE DERIVATIVE; HYDROGEN; METHYL GROUP; TETRAHYDROFURAN DERIVATIVE; TRIACETIN;

CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; HALF LIFE TIME; LETTER; PHOTOLYSIS; STEREOCHEMISTRY; SYNTHESIS; THERMOSTABILITY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0033520792     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991387c     Document Type: Letter

References (25)

1. Igau, A.; Grutzmacher, H.; Baceiredo, A.; Bertrand G. J. Am. Chem. Soc. 1988, 110, 6463. See also: Alcaraz, G.; Wecker, U.; Baceiredo, A.; Dahan, F., Bertrand, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1246 and references therein.
2. Igau, A.; Grutzmacher, H.; Baceiredo, A.; Bertrand G. J. Am. Chem. Soc. 1988, 110, 6463. See also: Alcaraz, G.; Wecker, U.; Baceiredo, A.; Dahan, F., Bertrand, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1246 and references therein.
3. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361. See also: Arduengo, A. J., III; Krafczyk, R. Chem. Z. 1998, 32, 6, and references therein.
4. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361. See also: Arduengo, A. J., III; Krafczyk, R. Chem. Z. 1998, 32, 6, and references therein.
5. For a recent review, see: Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
6. (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 674.
7. (b) Dagani, R. Chem. Eng. News 1991, Jan 28, 19. Dagani, R. Chem. Eng. News 1994, May 2, 20.
8. (b) Dagani, R. Chem. Eng. News 1991, Jan 28, 19. Dagani, R. Chem. Eng. News 1994, May 2, 20.
9. (c) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023.
10. (d) Boehme, C.; Frenking, G. J. Am. Chem. Soc. 1996, 118, 2039.
11. (a) Tomioka, H.; Hattori, M., Hirai, K.; Murata, S. J. Am. Chem. Soc. 1996, 118, 8723.
12. (b) See for a review: Tomioka, H. Acc. Chem. Res. 1997, 30, 315. Tomioka, H. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 2, pp 175-214.
13. (b) See for a review: Tomioka, H. Acc. Chem. Res. 1997, 30, 315. Tomioka, H. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 2, pp 175-214.
14. (a) Tomioka, H.; Nakajima, J.; Mizuno, H.; Sone, T.; Hirai, K. J. Am. Chem. Soc. 1995, 117, 11355.
15. (b) Tomioka H.; Hattori, M.; Hirai, K.; Sone, K.; Shiomi, D.; Takui, T.; Ithoh, K. J. Am. Chem. Soc. 1998, 120, 1106.
16. (c) Tomioka, H.; Mizuno, H.; Itakura, H.; Hirai, K. J. Chem. Soc., Chem. Commun. 1997, 2261.
17. See for instance: Tomioka, H.; Taketsuji, K. J. Chem. Soc., Chem. Commun. 1997, 1745.
18. 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. Tukada, H.; Sugawara, T.; Murata, S.; Iwamura, H. Tetrahedron Lett. 1986, 27, 235.
19. 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. Tukada, H.; Sugawara, T.; Murata, S.; Iwamura, H. Tetrahedron Lett. 1986, 27, 235.
20. See for reviews: (a) Trozzolo, A. M. Acc. Chem. Res. 1968, 1, 329. (b) Trozzolo, A. M.; Wasserman, E. In Carbenes; Moss, R. A., Jones, M., Jr., Eds.; Wiley: New York, 1975; Vol. 2, Chapter 5. (c) Sander, W.; Bacher, G.; Weirlacher, S. Chem. Rev. 1993, 93, 1593.
21. See for reviews: (a) Trozzolo, A. M. Acc. Chem. Res. 1968, 1, 329. (b) Trozzolo, A. M.; Wasserman, E. In Carbenes; Moss, R. A., Jones, M., Jr., Eds.; Wiley: New York, 1975; Vol. 2, Chapter 5. (c) Sander, W.; Bacher, G.; Weirlacher, S. Chem. Rev. 1993, 93, 1593.
22. See for reviews: (a) Trozzolo, A. M. Acc. Chem. Res. 1968, 1, 329. (b) Trozzolo, A. M.; Wasserman, E. In Carbenes; Moss, R. A., Jones, M., Jr., Eds.; Wiley: New York, 1975; Vol. 2, Chapter 5. (c) Sander, W.; Bacher, G.; Weirlacher, S. Chem. Rev. 1993, 93, 1593.
23. It is well-documented that diarylcarbenes with triplet ground states are readily trapped by oxygen to generate the corresponding diaryl ketone oxides. For a review, see: Sander W. Angew. Chem., Int. Ed. Engl. 1990, 20, 344.
24. It is also well-documented that triplet diarylcarbenes generated in the presence of good hydrogen donor undergo H abstraction leading to the corresponding radical showing transient absorption at longer wavelength than the corresponding carbene. For reviews see: Platz, M. S., Ed. Kinetics and Spectroscopy of Carbenes and Biradicals; Plenum: New York, 1990. Jackson, J. E.; Platz, M. S. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, pp 87-160.
25. It is also well-documented that triplet diarylcarbenes generated in the presence of good hydrogen donor undergo H abstraction leading to the corresponding radical showing transient absorption at longer wavelength than the corresponding carbene. For reviews see: Platz, M. S., Ed. Kinetics and Spectroscopy of Carbenes and Biradicals; Plenum: New York, 1990. Jackson, J. E.; Platz, M. S. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, pp 87-160.