On the mechanism of the stereo- and regioselective ether-ring opening of 1,2,3,4-tetrahydro-1β,4β-epoxy-2α,3α-carbonyldioxy arene systems with boron tribromide

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3651-3654

  Gopalaswamy, Ramesh ^a   Koreeda, Masato ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; THEORY;

ARENE;

EID: 0030010001     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00664-8     Document Type: Article

References (10)

1. (a) Harvey, R. G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, UK; 1991.
2. (b) Osborne, M. R.; Crosby, N. T. Benzopyrenes; Cambridge University Press, Cambridge, UK; 1987.
3. Harvey, R. G. In Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G., Ed.; American Chemical Society Symposium Series 283; American Chemical Society: Washington, D. C., 1985; pp 35-62.
4. (a) Koreeda, M.; Jung, K.-Y.; Hirota, M. J. Am. Chem. Soc. 1990, 112, 7413.
5. (b) Koreeda, M.; Gopalaswamy, R. G. Ibid. 1995, 117, 10595.
6. Jerina, D. M.; Yagi, H.; Lehr, R. E.; Thakker, D. R.; Schaefer-Ridder, M.; Karle, J. M.; Levin, W.; Wood, A. W.; Chang, R. L.; Conney, A. H. In Polycyclic Hydrocarbons and Cancer; Gelboin, H. V.; T'so, P. O. P., Eds.; Academic Press: New York; 1978; Vol. 1, pp 173-188 and references cited therein.
7. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
8. Stewart, J. J. P. QCPE 1990, 10, 9 and 1985, 5, 455.
9. 6. Stewart, J. J. P. QCPE 1990, 10, 9 and 1985, 5, 455.
10. The lowest-energy conformations of the tetrahydrobenzo ring in D in all of the bay-region containing PAH systems examined have been calculated to adopt the boat forms as indicated in Scheme 2. Therefore, the transition state for the transformation C → D is likely to resemble a boat form rather than the half-chair form for the tetrahydrobenzo ring as postulated in our earlier publication (see Ref 3a).