Friedel-crafts cyclization of 1,1-difluoroalk-1-enes: Synthesis of benzene-fused cyclic ketones via α-fluorocarbocations

Synthesis

Volumn , Issue 1, 2005, Pages 39-46

  Ichikawa, Junji ^a   Jyono, Hideharu ^b   Kudo, Takao ^b   Fujiwara, Masaki ^a   Yokota, Misaki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

fluorocarbocation; Bicyclic ketone; Difluoroalkene; Fluoroalcohol solvent; Friedel Crafts cyclization

Indexed keywords

BENZENE; HYDROLYSIS; KETONES; PHENOLIC RESINS;

1,1-DIFLUOROALK-1-ENES; BICYCLIC KETONES; FRIEDEL-CRAFTS CYCLIZATION;

SYNTHESIS (CHEMICAL);

2,2,2 TRIFLUOROETHYL 4 TOLUENESULFONATE; ALCOHOL; ALKENE DERIVATIVE; BENZENE; BICYCLO COMPOUND; FLUOROCARBON; KETONE; PHENYL GROUP; SOLVENT; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLIZATION; FRIEDEL CRAFTS REACTION; HYDROLYSIS; SYNTHESIS;

EID: 12344252921     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834910     Document Type: Article

References (34)

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28. For recent examples, see: (a) Vukics, K.; Fodor, T.; Fischer, J.; Fellegvári, I.; Lévai, S. Org. Process Res. Dev. 2002, 6, 82. (b) Suh, Y.-G.; Shin, D.-Y.; Min, K.-K.; Hyun, S.-S.; Jung, J.-K.; Seo, S.-Y. Chem. Commun. 2000, 1203 . (c) Deshpande, M. N.; Cain, M. H.; Patel, S. R.; Singam, P. R.; Brown, D.; Gupta, A.; Barkalow, J.; Callen, G.; Patel, K.; Koops, R.; Chorghade, M.; Foote, H.; Pariza, R. Org. Process Res. Dev. 1998, 2, 351. (d) Geen, G. R.; Mann, I. S.; Mullane, M. V.; McKillop, A. Tetrahedron 1998, 54, 9875. (e) Sugimoto, H.; Iimura, Y.; Yamanishi, Y.; Yamatsu, K. J. Med. Chem. 1995, 38, 4821.
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30. 34 = 11.9 Hz). Moreover, the observed NOEs between the C-2 axial proton and the methyl proton of the major isomer and between the C-2 axial proton and the C-4 axial proton of the minor isomer support this assignment. Stereochemistry was assigned for 2g on the basis of the proton coupling constants in a similar manner.
31. 19F NMR measurement of the reaction mixture.
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34. 1H FT NMR Spectra; Aldrich Chemical Company, Inc.: Milwaukee, 1992. (b) Pouchert, C. J. The Aldrich Library of Infrared Spectra 3rd ed.; Aldrich Chemical Company, Inc.: Milwaukee, 1981.