Diphenylmethylchlorocarbene: Comparison of experiment and theory

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5101-5104

  Moss, Robert A ^a   Wei, Ma ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE DERIVATIVE; DIPHENYLMETHYLCHLOROCARBENE; UNCLASSIFIED DRUG;

ARTICLE; COMPARATIVE STUDY; CONTROLLED STUDY; EXPERIMENT; KINETICS; MIGRATION; THEORY;

EID: 0033538598     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00879-5     Document Type: Article

References (32)

1. Reviews: (a) Moss, R. A. Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI: Greenwich, 1994; Vol. 1, pp. 59f.
2. (b) Bonneau, R.; Liu, M. T. H. Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI: Stamford, 1998; Vol. 2, pp. 1f.
3. (c) Platz, M. S. Ibid. pp. 133f.
4. (d) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287.
5. (a) Bonneau, R.; Liu, M. T. H.; Rayez, M. T. J. Am. Chem. Soc. 1989, 111, 5973.
6. (b) Liu, M. T. H.; Bonneau, R. Ibid. 1989, 111, 6873.
7. (c) La Villa, J. A.; Goodman, J. L. Ibid. 1989, 111, 6877.
8. (d) Liu, M. T. H.; Bonneau, R. Ibid. 1990, 112, 3915.
9. (e) Jackson, J. E.; Soundararajan, N.; White, W.; Liu, M. T. H.; Bonneau, R.; Platz, M. S. Ibid. 1989, 111, 6874.
10. (f) Bonneau, R.; Liu, M. T. H.; Kim, K. C.; Goodman, J. L. Ibid. 1996, 118, 3829.
11. (g) Wierlacher, S.; Sander, W.; Liu, M. T. H. Ibid. 1993, 115, 8943.
12. (h) Merrer, D. C.; Moss, R. A.; Liu, M. T. H.; Banks, J. T.; Ingold, K. U. J. Org. Chem. 1998, 63, 3010.
13. (i) Liu, M. T. H.; Bonneau, R. J. Am. Chem. Soc. 1996, 118, 8098.
14. A 'spectator' substituent is bonded to the carbenic carbon where it alters the electronic environment and reactivity of this migration terminus for a 1,2-rearrangement.
15. Moss, R. A.; Xue, S.; Liu, W.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1996, 118, 12588.
16. (a) Moss, R. A.; Xue, S.; Ma, W.; Ma, H. Tetrahedron Lett. 1997, 38, 4379.
17. (b) Moss, R. A.; Merrer, D. C. Ibid. 1998, 39, 8067.
18. Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Phys. Chem. A 1998, 102, 8467.
19. A 'bystander' substituent is bound to the migration origin and influences the efficiency of a rearrangement arising at that site.8
20. Nickon, A. Acc. Chem. Res. 1993, 26, 84.
21. Kenar, J. A.; Nickon, A. Tetrahedron 1997, 53, 14871.
22. 2h but the Ph shift product may come from the excited diazirine (see below) precursor of 3. Ph shift does not occur with thermally generated 3 (isooctane, 78°C).
23. Graham, W. H. J. Am. Chem. Soc. 1965, 87, 4396.
24. Garigipati, R. S. Tetrahedron Lett. 1990, 31, 1969.
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26. Kamigata, N.; Satoh, T.; Yoshida, M.; Kobayashi, M. Chem. Lett. 1987, 345.
27. 5 in benzene gave 52% of (E,Z)-9, Z/E=4.3, identified by GC-MS and NMR; cf, Kropp, P. J.; Crawford, S. D. J. Org. Chem. 1994, 59, 3102.
28. Nigam, M.; Platz, M. S.; Showalter, B. M.; Toscano, J. P.; Johnson, R.; Abbot, S. C.; Kirchhof, M. M. J. Am. Chem. Soc. 1998, 120, 8055.
29. Moss, R. A.; Ho, G.-J. J. Phys. Org. Chem. 1993, 6, 126.
30. White III, W. R.; Platz, M. S. J. Org. Chem. 1992, 57, 2841.
31. La Villa, J, A.; Goodman, J. L. Tetrahedron Lett. 1990, 31, 5109.
32. Jackson, J. E.; Soundararajan, N.; Platz, M. S.; Liu, M. T. H. J. Am. Chem. Soc. 1998, 110, 5595.