Stepwise mechanisms in cyclopropylcarbene reactions

Journal of the American Chemical Society

Volumn 120, Issue 26, 1998, Pages 6473-6476

  Cummins, Jordan M ^a   Porter, Timothy A ^a   Jones Jr , Maitland ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC COMPOUND; POLYENE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MOLECULAR DYNAMICS; REACTION ANALYSIS;

EID: 0032496949     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9803052     Document Type: Article

References (25)

1. Jones, M, Jr.; Reich, S. D.; Scott, L. S. J. Am. Chem. Soc. 1970, 92, 3118.
2. (a) For a summary of the chemistry of cyclopropylcarbenes see: Arct, J.; Brinker, U. H. In Methoden der Organische Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme Verlag: Stuttgart, 1989; Vol. E19b, pp 337-375.
3. (b) Specific examples of investigations of stereochemistry can be found in: Guarino, A.; Wolf, A. P. Tetrahedron Lett. 1969, 655. Berson, J. A.; Bauer, W.; Campbell, M. M. J. Am. Chem. Soc. 1970, 92, 7515. Sohn, M. B. Ph.D. Thesis, Princeton University, 1972, Bergman, R. G.; White, D. H. Private communication, 1972. Olin, S. S.; Venable, R. M. J. Chem. Soc., Chem. Commun. 1974, 273. Gallucci, R. R.; Jones, M., Jr. J. Am. Chem. Soc. 1976, 98, 7704.
4. (b) Specific examples of investigations of stereochemistry can be found in: Guarino, A.; Wolf, A. P. Tetrahedron Lett. 1969, 655. Berson, J. A.; Bauer, W.; Campbell, M. M. J. Am. Chem. Soc. 1970, 92, 7515. Sohn, M. B. Ph.D. Thesis, Princeton University, 1972, Bergman, R. G.; White, D. H. Private communication, 1972. Olin, S. S.; Venable, R. M. J. Chem. Soc., Chem. Commun. 1974, 273. Gallucci, R. R.; Jones, M., Jr. J. Am. Chem. Soc. 1976, 98, 7704.
5. (b) Specific examples of investigations of stereochemistry can be found in: Guarino, A.; Wolf, A. P. Tetrahedron Lett. 1969, 655. Berson, J. A.; Bauer, W.; Campbell, M. M. J. Am. Chem. Soc. 1970, 92, 7515. Sohn, M. B. Ph.D. Thesis, Princeton University, 1972, Bergman, R. G.; White, D. H. Private communication, 1972. Olin, S. S.; Venable, R. M. J. Chem. Soc., Chem. Commun. 1974, 273. Gallucci, R. R.; Jones, M., Jr. J. Am. Chem. Soc. 1976, 98, 7704.
6. (b) Specific examples of investigations of stereochemistry can be found in: Guarino, A.; Wolf, A. P. Tetrahedron Lett. 1969, 655. Berson, J. A.; Bauer, W.; Campbell, M. M. J. Am. Chem. Soc. 1970, 92, 7515. Sohn, M. B. Ph.D. Thesis, Princeton University, 1972, Bergman, R. G.; White, D. H. Private communication, 1972. Olin, S. S.; Venable, R. M. J. Chem. Soc., Chem. Commun. 1974, 273. Gallucci, R. R.; Jones, M., Jr. J. Am. Chem. Soc. 1976, 98, 7704.
7. (b) Specific examples of investigations of stereochemistry can be found in: Guarino, A.; Wolf, A. P. Tetrahedron Lett. 1969, 655. Berson, J. A.; Bauer, W.; Campbell, M. M. J. Am. Chem. Soc. 1970, 92, 7515. Sohn, M. B. Ph.D. Thesis, Princeton University, 1972, Bergman, R. G.; White, D. H. Private communication, 1972. Olin, S. S.; Venable, R. M. J. Chem. Soc., Chem. Commun. 1974, 273. Gallucci, R. R.; Jones, M., Jr. J. Am. Chem. Soc. 1976, 98, 7704.
8. (b) Specific examples of investigations of stereochemistry can be found in: Guarino, A.; Wolf, A. P. Tetrahedron Lett. 1969, 655. Berson, J. A.; Bauer, W.; Campbell, M. M. J. Am. Chem. Soc. 1970, 92, 7515. Sohn, M. B. Ph.D. Thesis, Princeton University, 1972, Bergman, R. G.; White, D. H. Private communication, 1972. Olin, S. S.; Venable, R. M. J. Chem. Soc., Chem. Commun. 1974, 273. Gallucci, R. R.; Jones, M., Jr. J. Am. Chem. Soc. 1976, 98, 7704.
9. Sasaki, T.; Eguchi, S.; Ohno, M.; Umemura, T. J. Org. Chem. 1973, 38, 4095.
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11. Schoeller, W. W. J. Org. Chem. 1980, 45, 2161. Armstrong, B. M.; McKee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685.
12. (a) Thamattoor, D. M.; Jones, M., Jr.; Pan, W.; Shevlin, P. B. Tetrahedron Lett. 1996, 37, 8333.
13. (b) Huang, H.; Platz, M. S. Tetrahedron Lett. 1996, 37, 8337.
14. We are redoing the stereochemical experiments starting from hydrocarbon carbene sources. Ruck, R. R. Unpublished work.
15. If you do not mind doing a distillation of several hundred grams of naphthalene!
16. Glick, H.; Likhotvorik, I. R.; Jones, M., Jr. Tetrahedron Lett. 1995, 36, 5715 and references therein.
17. Gunther, H.; Skyoakh, A.; Cremer, D.; Frisch, K.-H. Justus Liebigs Ann. Chem. 1978, 150.
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19. Hales, N. J.; Heany, H.; Hollinshead, J. H.; Singh, P. Org. Syn. 1980, 59, 71.
20. We thank Dr. John Eng for assistance with this measurement.
21. Redmond, K.; Carpenter, B. K. J. Org. Chem. 1997, 62, 5668.
22. Paquette, L. A.; Meisinger, R. H.; Wingard, R. E., Jr. J. Am. Chem. Soc. 1972, 94, 9224.
23. For earlier work on this system, see: Dauben, W. G.; Michno, D. M. J. Am. Chem. Soc. 1981, 103, 2284.
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25. Doering, W. v. E.; Goldstein, M. J. Tetrahedron, 1959 5, 53.