Activation parameters for additions of ambiphilic methoxychlorocarbene to alkenes

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4045-4048

  Moss, Robert A ^a   Zhang, Min ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349179431     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801575v     Document Type: Article

References (31)

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2. Zupancic, J. J.; Schuster, G. B. J. Am. Chem. Soc. 1980, 102, 5958.
3. Turro, N. J.; Lehr, G. F.; Butcher, J. A., Jr.; Moss, R. A.; Guo, W. J. Am. Chem. Soc. 1982, 104, 1754.
4. Zupancic, J. J.; Schuster, G. B. J. Am.Chem. Soc. 1981, 103, 944.
5. Moss, R. A.; Lawrynowicz, W.; Turro, N. J.; Gould, I. R.; Cha, Y. J. Am. Chem. Soc. 1986, 108, 7028.
6. For reviews of this early work, see: (a) Moss, R. A. Acc. Chem. Res. 1989, 22, 15.
7. (b) Moss, R. A.; Turro, N. J. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; p 213f.
8. Skell, P. S.; Cholod, M. S. J. Am. Chem. Soc. 1969, 91, 7131.
9. (a) Houk, K. N.; Rondan, N. G.; Mareda, J. Tetrahedron 1985, 41, 1555.
10. (b) Houk, K. N.; Rondan, N. G.; Mareda, J. J. Am. Chem. Soc. 1984, 106, 4291.
11. (c) Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 4293.
12. Blake, J. F.; Wierschke, S. G.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 1919.
13. (a) Giese, B.; Meister, J. Angew. Chem., Int. Ed. Engl. 1978, 17, 595.
14. (b) Giese, B.; Lee, W.-B. Angew. Chem., Int. Ed. Engl. 1980, 19, 835.
15. (c) Giese, B.; Lee, W.-B.; Meister, J. Ann. Chem. 1980, 725.
16. (d) Giese, B.; Lee, W.-B. Chem. Ber. 1981, 114, 3306.
17. Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770.
18. Moss, R. A.; Wang, L.; Zhang, M.; Skalit, C.; Krogh-Jespersen, K. J. Am. Chem. Soc. 2008, 130, 5634.
19. ≠ (-2.3 and -1.8 kcal/mol, respectively).
20. (a) Moss, R. A.; Fedorynski, M.; Shieh, W.-C. J. Am. Chem. Soc. 1979, 101, 4736.
21. (b) Moss, R. A. Acc. Chem. Res. 1980, 13, 58.
22. Moss, R. A.; Ge, C.-S.; Wlostowska, J.; Jang, E. G.; Jefferson, E. A.; Fan, H. Tetrahedron Lett. 1995, 36, 3083.
23. Moss, R. A. In Carbenes; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1973; Vol. 1, p 153f.
24. Graham, W. H. J. Am. Chem. Soc. 1965, 87, 4396.
25. Jackson, J. E.; Soundararajan, N.; Platz, M. S.; Liu, M. T. H. J. Am. Chem. Soc. 1988, 110, 5595.
26. Ge, C.-S.; Jang, E. G.; Jefferson, E. A.; Liu, W.; Moss, R. A.; Wlostowska, J.; Xue, S. Chem. Commun. 1994, 1479. In DCE, the MeOCCl-pyridine ylide signal is stable for at least 2 μs.
27. See, for example: Moss, R. A.; Tian, J.; Sauers, R. R.; Skalit, C.; Krogh-Jespersen, K. Org. Lett. 2007, 9, 4053.
28. UV analysis indicated that the diazirine was absent after 3 h of photolysis.
29. 14a,15 cyclopropanes as indicators of identity and reaction efficiency.
30. Moss, R. A.; Fan, H.; Hadel, L. M.; Shen, S.; Wlostowska, J.; Wlostowski, M.; Krogh-Jespersen, K. Tetrahedron Lett. 1987, 28, 4779.
31. Krogh-Jespersen, K.; Moss, R. A. Work in progress. At this time, the computational and experimental results are not fully congruent. It therefore seems preferable to reserve a comparative discussion for the full paper.