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Abstract:

The UV irradiation of 2,3-diphenylindoles produces two photochemical reactions: a dehydrocyclization with formation of dibenzocarbazoles and a photo-oxygenation which yields benzophenones. Substituents on the 2,3-diphenylindole have a great influence on the reaction course and in most of the examples here studied only one product was formed. Some considerations about the excited states involved in these reactions are presented. © 1974.

Registro:

Documento: Artículo
Título:Photochemical reactions of 2,3-diphenylindoles
Autor:Mudry, C.A.; Frasca, A.R.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellón II, Ciudad Universitaria, Buenos Aires, Argentine
Año:1974
Volumen:30
Número:17
Página de inicio:2983
Página de fin:2991
DOI: http://dx.doi.org/10.1016/S0040-4020(01)97543-X
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v30_n17_p2983_Mudry

Referencias:

  • Mudry, Frasca, (1973) Tetrahedron, 29, p. 603
  • Blackburn, Timmons, (1969) Quart. Rev., 23, p. 482
  • Padwa, Hartman, (1966) J. Am. Chem. Soc., 88, p. 3759
  • Wynberg, van Driel, Kellogg, Buter, (1967) J. Am. Chem. Soc., 89, p. 3487
  • Cooper, Wasserman, Photolysis of 4,5-diphenyl-oxazoles, -thiazoles, and -imidazoles. Formation of phenanthro[9,10-d]-heterocyclic systems (1969) Journal of the Chemical Society D: Chemical Communications, p. 200
  • Szmuszkovicz, 3,6-DIMETHOXY-9H- DIBENZO[a,c]CARBAZOLE (1969) Organic Preparations and Procedures, 1, p. 105
  • Mallory, Wood, Gordon, (1964) J. Am. Chem. Soc., 86, p. 3094
  • Kasha, (1950) Dis. Faraday Soc., 9, p. 14
  • Blackburn, Timmons, (1970) J. Chem. Soc. (C), p. 172
  • Kearns, (1971) Chem. Rev., 71, p. 395
  • Da Settimo, Saettone, (1965) Tetrahedron, 21, p. 823
  • Grammaticakis, (1952) C. R. Acad Sci., Paris, 235, p. 546
  • Ritchie, (1946) J. Proc. Roy. Soc. N.S. Wales, 80, p. 33
  • Richards, (1910) J. Chem. Soc., 97, p. 977
  • Ockenden, Schofield, 124. Indoles. Part III. The action of (A) ozone, and (B) osmium tetroxide on some indole derivatives (1953) Journal of the Chemical Society (Resumed), p. 612

Citas:

---------- APA ----------
Mudry, C.A. & Frasca, A.R. (1974) . Photochemical reactions of 2,3-diphenylindoles. Tetrahedron, 30(17), 2983-2991.
http://dx.doi.org/10.1016/S0040-4020(01)97543-X
---------- CHICAGO ----------
Mudry, C.A., Frasca, A.R. "Photochemical reactions of 2,3-diphenylindoles" . Tetrahedron 30, no. 17 (1974) : 2983-2991.
http://dx.doi.org/10.1016/S0040-4020(01)97543-X
---------- MLA ----------
Mudry, C.A., Frasca, A.R. "Photochemical reactions of 2,3-diphenylindoles" . Tetrahedron, vol. 30, no. 17, 1974, pp. 2983-2991.
http://dx.doi.org/10.1016/S0040-4020(01)97543-X
---------- VANCOUVER ----------
Mudry, C.A., Frasca, A.R. Photochemical reactions of 2,3-diphenylindoles. Tetrahedron. 1974;30(17):2983-2991.
http://dx.doi.org/10.1016/S0040-4020(01)97543-X