Mechanistic studies of the free-radical fragmentation of monoalkyl diazenes

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6569-6572

  Myers, Andrew G ^a   Movassaghi, Mohammad ^a   Zheng, Bin ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; FREE RADICAL;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; TECHNIQUE;

EID: 0030820288     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01497-4     Document Type: Article

References (19)

1. (a) Myers, A. G.; Movassaghi, M.; Zheng, B., submitted for publication in J. Am. Chem. Soc.
2. (b) For the preparation of NBSH, see: Myers, A. G.; Zheng, B.; Movassaghi, M., submitted for publication in J. Org. Chem.
3. (a) Kosower, E. M. Acc. Chem. Res. 1971, 4, 193.
4. (b) Tsuji, T.; Kosower, E. M. J. Am. Chem. Soc. 1971, 93, 1992.
5. Newcomb, M. Tetrahedron 1993, 49, 1151.
6. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739.
7. Citterio A.; Arnoldi, A.; Minisci, F. J. Org. Chem. 1979, 44, 2674.
8. (a) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 4.1, pp 715-777.
9. (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
10. (a) Gibanel, F.; López, M. C.; Royo, F. M.; Santafé, J.; Urieta, J. S. J. Solution Chem. 1993, 22, 211.
11. (b) Wilhem, E.; Battino, R. Chem. Rev. 1973, 73, 1.
12. (a) Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 5095.
13. (b) Dingledy, D. P.; Calvert, J. G. J. Am. Chem. Soc. 1963, 85, 856.
14. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1988, 53, 1629.
15. For other examples of TEMPO functioning as a radical-propagating agent, see: (a) Mahoney, L. R.; Mendennall, G. D.; Ingold, K. U. J. Am. Chem. Soc. 1973, 95, 8610.
16. (b) Connolly, T. J.; Scaiano, J. C. Tetrahedron Lett. 1997, 38, 1133.
17. Calculations suggest that the barrier for fragmentation of methyl diazenyl radical to methyl radical and dinitrogen is ≤2.3 kcal/mol. (a) North, S. W.; Longfellow, C. A.; Lee, Y. T. J. Chem. Phys. 1993, 99, 4423.
18. (b) Andrews, B. K.; Weisman, R. B. J. Chem. Phys. 1994, 101, 6776.
19. (c) Hu, C.-H.; Schaefer, H. F., III J. Phys. Chem. 1995, 99, 7507.