A novel and efficient ceric ammonium nitrate catalyzed oxidative nuclear chlorination of activated aromatic compounds by acetyl chloride

Synlett

Volumn , Issue 2, 2003, Pages 221-222

  Roy, Subhas Chandra ^a   Rana, Kalyan Kumar ^a   Guin, Chandrani ^a   Banerjee, Biplab ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Acetyl chloride; Ceric ammonium nitrate; Nuclear chlorination

Indexed keywords

ACETANILIDE; ACETIC ACID DERIVATIVE; AMMONIUM NITRATE; ANILINE DERIVATIVE; ANISOLE; ANISOLE DERIVATIVE; AROMATIC COMPOUND; BENZENE DERIVATIVE; CERIUM NITRATE; N,N DIMETHYLANILINE; NAPHTHALENE; PARA XYLENE; TOLUENE;

ARTICLE; CATALYSIS; CATALYST; CHLORINATION; OXIDATION; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 0037284934     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-36783     Document Type: Article

References (19)

1. For a general review of aromatic halogenation, see: Braendlin, H. P.; McBee, E. T. In Friedel-Crafts and related reactions, Vol. III, part 2; Olah, G. A., Ed.; John Wiley and Sons, Inc.: New York, 1964, Chap. 46.
2. Krumenacker, L.; Ratton, S. L'actualite Chimique 1986, 6, 29.
3. March, J. Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1985, 576.
4. See for example: Kharasch, M. S.; Reinmuth, O. Grignard Reactions of Nonmetallic Substances; Prentice-Hall: New York, 1954.
5. De la Mare, P. B. D.; Suzuki, H. J. Chem. Soc. C 1967, 1586.
6. Campaigne, E.; Thompson, W. J. Am. Chem. Soc. 1950, 72, 629.
7. Chip, G. K.; Grossert, J. S. Can. J. Chem. 1972, 50, 1233.
8. Nonhebel, D. C. Org. Synth. 1963, 43, 15.
9. Kovacic, P.; Sparks, A. K. J. Am. Chem. Soc. 1960, 82, 5740.
10. Albeck, M.; Shaik, S. J. Chem. Soc., Perkin Trans. 1 1975, 1233.
11. Juenge, E. C.; Beal, D. A.; Duncan, W. P. J. Org. Chem. 1970, 35, 719.
12. Yaroslavsky, C.; Katchalski, E. Tetrahedron Lett. 1972, 5173.
13. (a) Kajigaeshi, S.; Kakinami, T.; Ikeda, H.; Okamoto, T. Chem. Express 1988, 3, 659.
14. (b) Kajigaeshi, S.; Shinmasu, Y.; Fujisaki, S.; Kakinami, T. Chem. Lett. 1989, 415.
15. (c) Kajigaeshi, S.; Ueda, Y.; Fujisaki, S.; Kakinami, T. Bull. Chem. Soc. Jpn. 1989, 62, 2096.
16. (d) Kajigaeshi, S.; Shinmasu, Y.; Fujisaki, S.; Kakinami, T. Bull. Chem. Soc. Jpn. 1990, 63, 941.
17. Roy, S. C.; Guin, C.; Rana, K. K.; Maiti, G. Tetrahedron Lett. 2001, 6941.
18. 4). Volatiles were removed under reduced pressure and the residue obtained was purified by column chromatography over silica gel (2% ethyl acetate in light petroleum) to yield the pure chlorinated product.
19. Dincturk, S.; Ridd, J. H. J. Chem. Soc., Perkin Trans. 2 1982, 965; and references cited therein.