Photorearrangement of 9,10-epoxy-9,10-dihydrophenanthrene. Synthesis of 2,3:4,5-dibenzoxepin

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 2, 1973, Pages 37-38

  Brightwell, N E ^a   Griffin, G W ^a  

^a LOUISIANA STATE UNIVERSITY HEALTH SCIENCES CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049141186     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39730000037     Document Type: Article

References (11)

1. R. B. Woodward and R. Hoffmann, ‘The Conservation of Orbital Symmetry,’ Academic Press, New York, 1970.
2. M. S. Newman and S. Blum, J. Amer. Chem. Soc., 1964, 86, 5598.
3. M. J. S. Dewar and N. Trinajstic, Tetrahedron, 1970, 26, 4269. Semi-empirical SCF MO calculations conducted by these investigators imply that annelation of benzene with the 3, 4 bond of oxepin should be extremely unfavourable and no members of this class of which (2) is representative are known.
4. G. W. Griffin, Angew. Chem. Internat. Edn., 1971, 10, 537.
5. G. W. Griffin, Angew. Chem., 1971, 83, 604.
6. D. R. Arnold and L. A. Karnischky, J. Amer. Chem. Soc., 1970, 92, 1404.
7. D. R. Arnold and L. A. Karnischky, ‘Organic Syntheses,’ Coll. vol. III, ed. E. C. Horning, Wiley, New York, 1955, p. 140.
8. W. A. Henderson, jun., R. Lopresti, and A. Zweig, J. Amer. Chem. Soc., 1969, 91, 6049.
9. E. Vogel and F.-G. Klarner, Angew. Chem. Internat. Edn., 1968, 7, 374.
10. J. A. Berson and M. R. Willcott, in, J. Amer. Chem. Soc., 1966, 88, 2494.
11. G. W. Gruber and M. Pomerantz, J. Amer. Chem. Soc., 1969, 91, 4004.