Abstract:
Chloro derivatives of N-methylcarbazole (1), N-phenylcarbazole (2), N-acetylcarbazole (3), N-benzoylcarbazole (4) and 2-methoxy-N-methylcarbazole are synthesized. They are compounds 1a, 1b, 1e, 1d, 1e, 2a, 2b, 3a, 3b, 3c, 3d, 4a, 4b, 5a, 5b, 5c, 5d and 5e. Some of them are described for the first time. By using semiempirical PM3 method theoretical substituent effects on the chlorinating reaction are calculated. A chlorination mechanism of carbazoles and N-substituted carbazoles are compared.
Referencias:
- Bonesi, S.M., Erra-Balsells, R., On the Synthesis and Isolation of Chlorocarbazoles Obtained by Chlorination of Carbazoles (1997) J. Heterocyclic Chem., , in press
- Erra-Balsells, R., Frasca, A.R., (1983) Tetrahedron, 39, p. 33
- Biondic, M.C., Erra-Balsells, R., (1990) J. Photochem. Photobiol. A: Chem., 51, p. 341
- Biondic, M.C., Erra-Balsells, R., (1992) J. Chem. Soc., Perkin Trans., 2, p. 1049
- Biondic, M.C., Erra-Balsells, R., (1993) J. Chem. Soc., Perkin Trans., 2, p. 887
- Biondic, M.C., Erra-Balsells, R., (1993) An. Asoc. Quim. Argent., 81, p. 403
- Biondic, M.C., Erra-Balsells, R., (1994) J. Photochem. Photobiol. A: Chem., 77, p. 149
- Biondic, M.C., Erra-Balsells, R., Effect of Carbon Tetrachloride on the Photobehaviour of Β-Carbolines, , unpublished results
- Erra-Balsells, R., Frasca, A.R., (1984) Tetrahedron, 25, p. 5363
- Erra-Balsells, R., Frasca, A.R., (1985) An. Asoc. Quim. Argent., 73, p. 201
- Bonesi, S.M., Erra-Balsells, R., (1991) J. Photochem. Photobiol. A: Chem., 56, p. 55
- Bonesi, S.M., Erra-Balsells, R., (1991) An. Asoc. Quim. Argent., 79, p. 113
- Bonesi, S.M., Erra-Balsells, R., (1991) J. Heterocyclic Chem., 28, p. 1035
- Bonesi, S.M., Erra-Balsells, R., Photochemistry of N-Acetylcarbazole: Photo-Fries Rearrangement and Photoinduced Single Electron Transfer, , submitted for publication
- Bonesi, S.M., Erra-Balsells, R., Photochemistry of N-Benzoylcarbazole: Photo-Fries Rearrangement and Photoinduced Single Electron Transfer, , submitted for publication
- Bonesi, S.M., Erra-Balsells, R., Effect of Halomethanes on the Photochemical Behaviour of Carbazoles, , unpublished results
- Coyle, J.D., (1986) Introduction to Organic Photochemistry, p. 1. , John Wiley and Sons, Great Britain
- Mattay, J., (1990) Photoinduced Electron Transfer I, Topics in Current Chemistry, p. 156. , Chapters 1, 2 and 3
- Fox, M.A., Chanon, M., (1988) Photoinduced Electron Transfer, , Elsevier, Amsterdam, Parts A-D
- Biswas, M., Das, S.K., (1982) Polymer., 23, p. 1713
- Biswas, M., Uryu, T., (1986) J. Macromol. Sci., Rev. Macromol. Chem., 26, p. 249
- (1966) Encyclopedia of Polymer Science and Technology, Part 5, , Interscience Publishers, John Wiley and Sons, Inc., New York
- Turro, N.J., (1978) Moderm Molecular Photochemistry, p. 76. , The Benjamin Cummings Publishing Company, Inc., California, Chapters 5 and 6
- Buu-Hoi, Ng.Ph., Royer, R., (1947) Rec. Trav. Chim. Pays Bas, 66, p. 533
- Mazzara, G., Lamberti-Zanardi, M., (1886) Gazz. Chim. Ital., 26, p. 239
- De la Mare, P.B.D., El Dusouqui, O.M.H., Johnson, E.A., (1966) J. Chem. Soc. B., p. 521
- De Rosa, M., Quesada, A., Dodsworth, D.J., (1987) J. Org. Chem., 52, p. 173
- (1994) HyperChem (TM) Release 4.5 for Windows, , Autodesk, Inc., Ontario
- Oikawa, Y., (1976) J. Org. Chem., 41, p. 1118
Citas:
---------- APA ----------
Bonesi, S.M. & Erra-Balsells, R.
(1997)
. On the Synthesis and Isolation of Chlorocarbazoles Obtained by Chlorination of N-Substituted Carbazoles. Journal of Heterocyclic Chemistry, 34(3), 891-900.
http://dx.doi.org/10.1002/jhet.5570340328---------- CHICAGO ----------
Bonesi, S.M., Erra-Balsells, R.
"On the Synthesis and Isolation of Chlorocarbazoles Obtained by Chlorination of N-Substituted Carbazoles"
. Journal of Heterocyclic Chemistry 34, no. 3
(1997) : 891-900.
http://dx.doi.org/10.1002/jhet.5570340328---------- MLA ----------
Bonesi, S.M., Erra-Balsells, R.
"On the Synthesis and Isolation of Chlorocarbazoles Obtained by Chlorination of N-Substituted Carbazoles"
. Journal of Heterocyclic Chemistry, vol. 34, no. 3, 1997, pp. 891-900.
http://dx.doi.org/10.1002/jhet.5570340328---------- VANCOUVER ----------
Bonesi, S.M., Erra-Balsells, R. On the Synthesis and Isolation of Chlorocarbazoles Obtained by Chlorination of N-Substituted Carbazoles. J. Heterocycl. Chem. 1997;34(3):891-900.
http://dx.doi.org/10.1002/jhet.5570340328