The carbazole connection: Unusual products from the diazotization of anthranilic acids

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6748-6750

  Qiao, Xiaoxin ^a   Ho, Douglas M ^a   Pascal Jr , Robert A ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001399603     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960949x     Document Type: Article

References (10)

1. Qiao, X.; Padula, M. A.; Ho, D. M.; Vogelaar, N. J.; Schutt, C. E.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1996, 118, 741-745.
2. Ogliaruso, M. A.; Romanelli, M. G.; Becker, E. I. Chem. Rev. 1965, 65, 261-367.
3. Wittig, G. Angew. Chem. 1957, 69, 245-251.
4. Berry, R. S.; Spokes, G. N.; Stiles, M. J. Am. Chem. Soc. 1962, 84, 3570-3577.
5. Logullo, F. M.; Seitz, A. H.; Friedman, L.; Abrams, G. D.; Ertl, H.; Yates, P. Organic Syntheses; Wiley: New York, 1973; Collect Vol. V, pp 54-59.
6. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IEZ, UK.
7. Other compounds observed included phenyl benzoate (3%), 2-nitrodiphenylamine (4%), acridone (20%), and N,O-diphenylanthranilate (23%). The identities of all but the last of these are based upon chromatographic and mass spectral comparisons of the reaction products with authentic standards; the structure of N,O-diphenylanthranilate is proposed on the basis of its mass spectral fragmentation pattern.
8. Ghosh, R.; Sheinin, E. B.; Bell, C. L.; Bauer, L. J. Heterocycl. Chem. 1975, 12, 203-206.
9. Miwa, T.; Kato, M.; Tamano, T. Tetrahedron Lett. 1968, 2743-2745.
10. Four isomers will result if one of the carbazole rings of 10 is derived from a diazonium-containing fragment, which must have the fluorine atom and diazonium group meta to each other, but only three isomers would be formed if the chlorofluoroaniline is derived from the diazonium-containing fragment. Of course, it may be that more than one pathway exists for the formation of 10.