Phenylation reaction of α-acylnitromethanes to give 1,2-diketone monooximes: Involvement of carbon electrophile at the position a to the nitro group

Synthesis

Volumn , Issue 24, 2009, Pages 4129-4136

  Takamoto, Mikihiro ^a   Kurouchi, Hiroaki ^a   Otani, Yuko ^a   Ohwada, Tomohiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

ketonitromethane; 1,2 dione monooxime; Electrophilic aromatic substitutions; Protonation; Umpolung

Indexed keywords

CARBOCATIONS; CARBON ELECTROPHILE; DIKETONES; ELECTROPHILES; ELECTROPHILIC AROMATIC SUBSTITUTIONS; GOOD YIELD; MONOOXIME; NITRO GROUP; PHENYLATION; TRIFLUOROMETHANE SULFONIC ACID; UMPOLUNG;

KETONES; PROTONATION;

AROMATIC COMPOUNDS;

1 NITRO 4 METHYLPENTA 2 ONE; 1 NITROBUTAN 2 ONE; 1,2 DIKETONE MONOOXIME DERIVATIVE; 3 CHLOROBENZILOXIME; 3 CHLOROBENZOYLNITROMETHANE; 3 TRIFLUOROMETHYLBENZILOXIME; 3 TRIFLUOROMETHYLBENZOYLNITROMETHANE; 4 BROMOBENZILOXIME; 4 BROMOBENZOYLNITROMETHANE; 4 CHLOROBENZILOXIME; 4 CHLOROBENZOYLNITROMETHANE; 4 METHOXYBENZILOXIME; 4 METHOXYBENZOYLNITROMETHANE; 4 METHYL 1 PHENYL 1,2 PENTANEDIONE 1 OXIME; 4 METHYLBENZILOXIME; 4 METHYLBENZOYLNITROMETHANE; 4 NITROBENZILOXIME; 4 NITROBENZOYLNITROMETHANE; 4 TRIFLUOROMETHYLBENZILOXIME; 4 TRIFLUOROMETHYLBENZOYLNITROMETHANE; ALPHA ACYLNITROMETHANE DERIVATIVE; BENZILMONOOXIME; BENZOYLNITROMETHANE; CARBON; METHANE; N (4 TRIFLUOROMETHYL)BENZOYLBENZOTRIAZOLE; N BENZOYLBENZOTRIAZOLE; OXIME; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; MELTING POINT; PHENYLATION; PROCESS OPTIMIZATION; PROTON TRANSPORT; REACTION TIME; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 78650727948     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217036     Document Type: Article

References (15)

1. Rosini, G. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991, Chap. 1.10, 321.
2. (a) Hawthorne, M. F. J. Am. Chem. Soc. 1957, 79, 2510.
3. (b) Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1965, 87, 1742.
4. (c) Kornblum, N.; Brown, R. A. J. Am. Chem. Soc. 1964, 86, 2681.
5. (d) Edward, J. T.; Tremaine, P. H. Can. J. Chem. 1971, 49, 3483.
6. Ohwada, T.; Yamagata, N.; Shudo, K. J. Am. Chem. Soc. 1991, 113, 1364.
7. Kearney, T.; Harris, P. A.; Jackson, A.; Joule, J. A. Synthesis 1992, 769.
8. Katritzky, A. R.; Zhang, Y.; Singh, S. K. Synthesis 2003, 2795.
9. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Gromova, A. V.; Witek, R.; Steel, P. J. J. Org. Chem. 2005, 70, 9211.
10. (a) Coustard, J.-M.; Jacquesy, J.-C.; Violeau, B. Tetrahedron Lett. 1991, 32, 3075.
11. (b) Coustard, J.-M.; Jacquesy, J.-C.; Violeau, B. Tetrahedron Lett. 1992, 33, 8085.
12. (c) Shimizu, T.; Hayashi, Y.; Teramura, K. Bull. Chem. Soc. Jpn. 1985, 58, 2519.
13. McMurry, J.; Melton, J. J. Org. Chem. 1973, 38, 4367
14. 3 group and the aromatic ortho-protons supported the assignment of the E-geometry of the olefin of 6b
15. The reaction of 2a also proceeded with substituted benzenes, p-xylene and anisole, to give the corresponding oximes in comparable yields (see ref 3).