The Photochemical Reaction of 1,1-dicyano-3-phenylbut-1-ene. Simultaneous Occurrence of π-methane and di-π-methane Rearrangements

Journal of the Brazilian Chemical Society

Volumn 10, Issue 5, 1999, Pages 375-380

  Da Silva, Francisco A ^a,b   Ferreira, Aurelio B B ^b   Neumann, Miguel G ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL RURAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

1,2 hydrogen photomigration; Di methane rearrangement; Organic photochemistry; methane rearrangement

Indexed keywords

EID: 0033272261     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Hixson, S.S. J. Chem. Soc., Chem. Commun. 1975, 515.
2. Akhtar, I.A.; McCullough, J.J.; Vaitekunas, S.; Faggiani, R.; Lock, C.J.L. Can. J. Chem. 1982, 60, 1657.
3. McCullough, J.J.; Manning, C. J. Org. Chem. 1978, 43, 2839.
4. Kumagai, T.; Segawa, T.; Endo, Z.; Mukai, T. Tetrahedron Lett. 1986, 27, 6225.
5. Zimmerman, H.E.; Sulzbach, H.M.; Tollefson, M.B. J. Am. Chem. Soc. 1993, 115, 6548.
6. Chen, J.; Scheffer, J.R.; Trotter, J. Tetrahedron 1992, 48, 3251.
7. Patrapan, S.; Ashok, K.; Gopidas, K.R.; Rath, N.P.; Das, P.K.; George, M.V. J. Org. Chem. 1990, 55, 1304.
8. Armesto, D.; Ortiz, M.J.; Roamno, S.; Agarrabeitia, A.R.; Ramos, A. J. Org. Chem. 1996, 61, 1459.
9. Mizobuchi, Y.; Miller, L.L. J. Org. Chem. 1985, 50, 318.
10. Zimmerman, H.E.; Angew. Chem. Int. Ed. Engl. 1969, 8, 1.
11. Zimmerman, H.E.; Mariano, P.S. J. Am. Chem. Soc. 1969, 91, 1718.
12. Griffin, G.W.; Covell, J.; Petterson, R.C.; Dodson, R.M.; Close, G. J. Am. Chem. Soc. 1965, 87, 1410.
13. Woodward, R.B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press; New York, p. 98-100, 1970.
14. Hixson, S.S. J. Am. Chem. Soc. 1976, 98, 1271.
15. Zimmerman, H.E.; Little, R.D. J. Am. Chem. Soc. 1974, 96, 5143.
16. Cookson, R.C.; Ferreira, A.B.B.; Salisbury, K. J. Chem. Soc., Chem. Commun. 1974, 665.
17. Adams, R. Organic Reactions; John Wiley, v. 15, p. 204, 1967.
18. Kruger, D.; Sopchik, A.E.; Kingsbury, C.A. J. Org. Chem. 1984, 49, 778.
19. Wolfe, J.; Berry, E.; Peterson, M.R. Can. J. Chem. 1976, 54, 210.
20. Ferreira, A.B.B.; Salisbury, K. J. Chem. Soc., Perkin Trans. 2, 1978, 995.
21. Barreau, M.; Bost, M.; Julia, M.; Lallemand, J.-Y. Tetrahedron Lett. 1975, 16, 3465.
22. De Keukeleire, E.C.; Sanford, E.C.; Hammond, G.S. J. Am. Chem. Soc. 1973, 95, 7904.
23. Zimmerman, H.E.; Steinmetz, M.G.; Kreil, C.L. J. Am. Chem. Soc. 1978, 100, 4146.
24. Zefirov, N.S.; Baranenkov, I.V. Tetrahedron Lett. 1979, 20, 4875.
25. Zimmerman, H.E.; Cotter, B.R. J. Am. Chem. Soc. 1974, 96, 7445.
26. Armesto, D.; Ramos, A.; Mayoral, E.P. Tetrahedron Lett. 1994, 35, 3785.