Remote substituent effects on phenylchlorocarbene C-H insertion reactions

Organic Letters

Volumn 1, Issue 5, 1999, Pages 819-822

  Moss, Robert A ^a   Yan, Shunqi ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011754515     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990161b     Document Type: Article

References (19)

1. Moss, R. A.; Yan, S. Tetrahedron Lett. 1998, 39, 9381.
2. (a) Seyferth, D.; Cheng, Y. M. J. Am. Chem. Soc. 1973, 95, 6763.
3. (b) Seyferth, D.; Mai, V. M.; Gordon, M. E. J. Org. Chem. 1970, 35, 1993.
4. Pascal, R. A., Jr.; Mischke, S. J. Org. Chem. 1991, 56, 6954.
5. Watanabe, H.; Ohsawa, N.; Sudo, T.; Hirakata, K.; Nagai, Y. J. Organomet. Chem. 1977, 128, 27.
6. Seyferth, D.; Damrauer, R.; Mui, J. Y.-P.; Jula, T. F. J. Am. Chem. Soc. 1968, 90, 2944.
7. Tabushi, I.; Yoshida, Z.; Takahashi, N. J. Am. Chem. Soc. 1970, 92, 6670.
8. Graham, W. H. J. Am. Chem. Soc. 1965, 87, 4396.
9. 2 azine. 4e could not be separated from excess 1e by chromatography and was identified in situ by GC-MS.
10. The insertion is 2-3 times slower in benzene than in pentane; benzene "complexes" PhCCl and modulates its reactivity: Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088. Krogh-Jespersen, K.; Yan, S.; Moss, R. A. J. Am. Chem. Soc. 1999, 121, 6269.
11. The insertion is 2-3 times slower in benzene than in pentane; benzene "complexes" PhCCl and modulates its reactivity: Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088. Krogh-Jespersen, K.; Yan, S.; Moss, R. A. J. Am. Chem. Soc. 1999, 121, 6269.
12. (a) Charton, M. Prog. Phys. Org. Chem. 1981, 13, 119.
13. (b) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
14. Owens, P. H.; Gleicher, G. J.; Smith, L. M., Jr. J. Am. Chem. Soc. 1968, 90, 4122.
15. Grob, C. A.; Fischer, W.; Katayama, H. Tetrahedron Lett. 1976, 2183 and references therein.
16. Exner, O.; Charton, M.; Galkin, V. J. Phys. Org. Chem. 1999, 12, 289 and accompanying papers.
17. GAUSSIAN 94, Revision E.2; Gaussian, Inc., Pittsburgh, PA, 1995.
18. 1
19. a for the PhCCl/Ad-H insertion is 9.1 kcal/mol, whereas the experimental value is 3.2 kcal/mol.