Synthesis of fused bicyclic rings by tandem radical ring expansion/cyclization: Evaluating competing intramolecular reactions

Tetrahedron

Volumn 54, Issue 29, 1998, Pages 8355-8370

  Wang, Cunxiao ^a   Gu, Xin ^a   Yu, Marvin S ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE; CYCLOPENTANONE DERIVATIVE;

ALKYLATION; ARTICLE; CYCLIZATION; GEOMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SYNTHESIS;

EID: 0032537673     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00467-0     Document Type: Article

References (22)

1. 1. (a) Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091.
2. (b) Curran, D. P. In Comprehensive Organic Synthesis; B. M. Trost and I. Fleming, Ed.; Pergamon: Oxford, 1991; Vol. 4; pp 779.
3. (c) Curran, D. P. Synlett 1991, 63.
4. 2. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442.
5. 3. Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365.
6. 4. Hollingworth, G. J.; Pattenden G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381.
7. 5. Similar hydrogen transfer reactions have been observed in different but related systems, a) Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3205.
8. b) Baldwin, J. E.; Adlington, R. M.; Singh, R. Tetrahedron 1992, 48, 3385.
9. 6. (a) Liotta, D.; Barnum, C.; Puleo, R.; Zima, G.; Bayer, C.; Kezar, H. S. J. Org. Chem. 1981, 46, 2920.
10. (b) Ley, S. V.; Murray, P. J.; Palmer, B. D. Tetrahedron 1985, 4765.
11. 7. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
12. 8. (a) Dowd, P.; Choi, S.-C. Tetrahedron, 1989, 77.
13. (b) Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565.
14. Recent kinetic studies on one-carbon ring expansions: c) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223.
15. d) Chatgilialoglu, C.; Timokhin, V. I.; Ballestri, M. J. Org. Chem. 1998, 63, 1327.
16. 9. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140.
17. 10. Kuehne, M. E. J. Org. Chem. 1970, 35, 171.
18. 11. Krapcho, A. P.; Diamanti, J.; Cayen, C.; Bingham, R. Org. Syn. 1967, 47, 20.
19. 12. We have not yet assigned the configurations of these products. Stereocontrol in the reactions of cycloheptyl radicals has not been well studied. See chapter 3 in Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: Weinheim, 1996.
20. 13. Newcomb, M. Tetrahedron 1993, 49, 1151. Rate constants were calculated from the second order rate equations in this paper.
21. 14. Taber, D.; Ruckle, R. E., Jr.; Hennessy, M. J. J. Org. Chem., 1986, 51, 4077.
22. 15. Taber, D.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686.