The nucleophilic reactivity of fluoromethoxycarbene

Organic Letters

Volumn 12, Issue 15, 2010, Pages 3476-3479

  Moss, Robert A ^a   Zhang, Min ^a   Krogh Jespersen, Karsten ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77955133411     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1013119     Document Type: Article

References (20)

1. For a review, see: Moss, R. A. Carbenic Philicity. In Carbene Chemistry from Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Dekker: New York, 2002; p 57f.
2. Moss, R. A.; Tian, J.; Sauers, R. R.; Ess, D. H.; Houk, K. N.; Krogh-Jespersen, K. J. Am. Chem. Soc. 2007, 129, 5167
3. Moss, R. A.; Tian, J.; Sauers, R. R.; Skalit, C.; Krogh-Jespersen, K. Org. Lett. 2007, 9, 4053
4. Moss, R. A.; Wang, L.; Krogh-Jespersen, K. J. Am. Chem. Soc. 2009, 131, 2128
5. For summaries, see: Moss, R. A.; Wang, L.; Zhang, M.; Skalit, C.; Krogh-Jespersen, K. J. Am. Chem. Soc. 2008, 130, 5634
6. Moss, R. A. J. Phys. Org. Chem. 2010, 23, 293
7. Moss, R. A.; Zhang, M. Org. Lett. 2008, 10, 4045
8. Moss, R. A.; Zhang, M.; Krogh-Jespersen, K. Org. Lett. 2009, 11, 1947
9. Moss, R. A. Acc. Chem. Res. 1980, 13, 58
10. Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770
11. Mitsch, R. A.; Neuvar, E. W.; Koshar, R. J.; Dybvig, D. H. J. Heterocycl. Chem. 1965, 2, 371
12. Moss, R. A. Acc. Chem. Res. 2006, 39, 267
13. Moss, R. A.; Fedorynski, M.; Terpinski, J.; Denney, D. Z. Tetrahedron Lett. 1986, 27, 419
14. 19F NMR data are included, along with mass spectra.
15. Moss, R. A. In Carbenes; Jones, M., Jr.; Moss, R. A., Eds.; Wiley: New York, 1973; Vol. 1, p 153f.
16. Analytical details appear in Table Tables S-1. The Supporting Information also includes GC traces of cyclopropanes 2-4.
17. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833
18. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899
19. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2005, 109, 5656
20. 2) employed here; large differences in computed and observed entropies of activation have been found in carbene additions conducted in pentane as well. (5a)