Steric control in the thermal rearrangement of a bicyclo[3.1.0]hex-2-ene substituted at a radical-nonstabilizing position

Journal of the American Chemical Society

Volumn 130, Issue 20, 2008, Pages 6430-6437

  Doering, William Von Eggers ^a   Zhao, Xin ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KINETIC PARAMETERS; THERMAL EFFECTS;

ARCHETYPE; DIRADICALS; STERIC CONTROL;

ORGANIC COMPOUNDS;

BICYCLO COMPOUND; HEXANE;

ARTICLE; CHEMICAL COMPOSITION; COMPRESSION; EQUILIBRIUM CONSTANT; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRESS STRAIN RELATIONSHIP; SUBSTITUTION REACTION; SURFACE PROPERTY; THERMODYNAMICS;

EID: 43949146272     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja7104812     Document Type: Article

References (24)

1. Baldwin, J. E.; Keliher, E. J. J. Am. Chem. Soc. 2002, 124, 380-381.
2. Doubleday, C., Jr.; Suhrada, C. P.; Houk, K. N J. Am. Chem. Soc. 2006, 128, 90-94.
3. It is suggested the reader be familiar with refs 1 and 2 before proceeding.
4. Simonsen, J. L. The Dicyclic Terpenes and their Derivatives, Vol. II, 2nd ed.; University Press: Cambridge, U.K., 1949; pp 10-16..
5. (a) Doering, W. v. E.; Lambert, J. B Tetrahedron 1963, 19, 1989-1994.
6. (b) Doering, W. v. E.; Schmidt, E. K. G Tetrahedron 1971, 27, 2005-2030.
7. (c) Doering, W. v. E.; Zhang, T.-h.; Schmidt, E. K. G. J. Org. Chem. 2006, 71, 5688-5693.
8. Swenton, J. S.; Wexler, A. J. J. Am. Chem. Soc. 1971, 93, 3066-3068.
9. (a) Grimme, W. cited in: Doering, W. von E.; Roth, W. R Angew. Chem., Int. Ed. Engl. 1963, 2, 115-122.
10. (b) Cooke, R. S.; Andrews, U. H. J. Am. Chem. Soc. 1974, 96, 2974-2980.
11. Monn, J. A.; Valli, M. J.; Massey, S. M.; Wright, R. A.; Salhoff, C. R.; Johnson, B. G.; Howe, T.; Alt, C. A.; Rhodes, G. A.; Robey, R. L.; Griffey, K. R.; Tizzano, J. P.; Kallman, M. J.; Helton, D. R.; Schoepp, D. D. J. Med. Chem. 1997, 528-537.
12. Young, W. G.; Winstein, S.; Goering, H. L. J. Am. Chem. Soc. 1951, 73, 1958-1963.
13. (a) Roth, W. R.; Fink, R.,unpublished,
14. (b) Marquardt, D. W. J. Soc. Ind. Appl. Math. 1963, 11, 431-441.
15. Doering, W. von E.; Keliher, E. J. J. Am. Chem. Soc. 2007, 129, 2488-2495.
16. Not having pure samples on hand, we have not determined GC response factors. In one instance analysis by GC and NMR were in excellent agreement.
17. - 1: methyl, 2.1; ethyl, 2.1; n-propyl, 2.0; isopropyl, 2.4; phenyl, 2.3; and tert-butyl, 6.1.
18. (a) Wolfgang, R.; MacKay, C. F. Nucleonics 1958, 16, 69-73.
19. (b) MacKay, C.; Wolfgang, R. J. Am. Chem. Soc. 1965, 148, 899-907.
20. Brown, H. C.; Fletcher, R. S. J. Am. Chem. Soc. 1949, 71, 1845-1854, and references therein.
21. Bartlett, P. D.; Tidwell, T. T. J. Am. Chem. Soc. 1968, 90, 4421-4428, and references therein.
22. (a) Doering, W. von E.; Sachdev, K. J. Am. Chem. Soc. 1974, 96, 1168-1187.
23. (b) Doering, W. von E.; Mastrocola, A. R. Tetrahedron, Suppl. 1 1981, 37, 329-344.
24. Payne, G. B. J. Org. Chem. 1967, 32, 3351-3355.