Solvent perturbs the reactivity of tert-butylcarbene

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2277-2280

  Ruck, Rebecca T ^a   Jones Jr , Maltland ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; MOLECULAR DYNAMICS; REACTION ANALYSIS;

EID: 0032537214     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00291-3     Document Type: Article

References (16)

1. 1. Support of this work by the National Science Foundation through grant CHE-9702823 is gratefully acknowledged. RTR thanks Pfizer, Inc. for a Pfizer Undergraduate Research Fellowship.
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3. 3. Cubbage, J. W.; Edelbach, B.L.; Kuen, K. S.; DeLuca, J. Tetrahedron 1997, 53, 9823.
4. 4. Kirmse, W. Carbene Chemisty, 2nd. Ed., Academic, New York, 1971, pp 422ff.
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8. 8. (a) Chang, K.-T.; Shechter, H. J. Am. Chem. Soc. 1979, 101, 5082.
9. (b) Glick, H.; Likhotvorik, I. R.; Jones, M. Jr Tetrahedron Lett. 1995, 36, 5715.
10. 9. For a recapitulation of the tert-butylcarbene story and relevant calculations, see: Armstrong, B. M.; McKee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685.
11. 10. March, J. Advanced Organic Chemistry, Wiley, New York, 1992, p 1054ff.,
12. 11. Aniline gives a ratio of 30:70. We suspect that protonation of, or hydrogen bonding to the carbene may be occurring.
13. 12. Friedman, L.; Shechter, H. J. Am. Chem. Soc. 1959, 61, 5512.
14. 13. Franzen, V.; Schmidt, H. J.; Mertz, C. Chem. Ber. 1961, 94, 2942.
15. 14. Schöllkopf, U.; Pitterhoff, W. Chem. Ber. 1964, 97, 636.
16. 15. For a summary, see reference 6, pp 108ff.