5,6-Dichlorohexafluorocyclohexa-1,3-dienes: Hexafluorobenzene Synthons

Journal of Organic Chemistry

Volumn 54, Issue 23, 1989, Pages 5511-5516

  Dailey, William P ^a   Correa, Ricardo A ^a   Harrison, Edwin ^a   Lemal, David M ^a  

^a DARTMOUTH COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HEXAFLUOROBENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0024790441     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00284a023     Document Type: Article

References (12)

1. This paper is based principally on the Ph.D. Dissertation of W. P. D., Dartmouth College, 1983.
2. Smart, B. E. In The Chemistry of Functional Groups, Supplement D: The Chemistry of Halides, Pseudohalides and Azides; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Part I.,pp 603–655. Hudlicky, M. Chemistry of Organic Fluorine Compounds, 2nd ed.; Halsted Press, Wiley: New York, 1976. Chambers, R. D. Fluorine in Organic Chemistry; Wiley: New York, 1973. Sheppard, W. A.; Sharts, C. M. Organic Fluorine Chemistry; Benjamin: New York, 1969.
3. Camaggi, G.; Gozzo, F.; Cevidalli, G. J. Chem. Soc., Chem. Commun. 1966. 313–314. Haller. I. J. Am. Chem. Soc. 1966. 88, 2070–1.
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5. Barlow, M. G.; Haszeldine, R. N.; Morton, W. D.; Woodward, D. R. J. Chem. Soc., Perkin Trans. I 1972, 2170–2180.
6. The difference is about 13 kcal/mol. March, J. Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York; p 23,624. March, J., ref 6a, p 624.
7. Russell, G. A. J. Am. Chem. Soc. 1968,80,4997, and earlier papers. See also: Skell, P. S.; Baxter, H. N.; Taylor, C. K. J. Am. Chem. Soc. 1983, 105, 120–1.
8. For other examples, see: Barefoot, A. C., III; Saunders, W. D.; Buzby, J. M.; Grayston, M. W.; Lemal, D. M. J. Org. Chem. 1980, 45, 4292–4295.
9. Bruce, M. I. J. Chem. Soc. 1968, 1459–1464.
10. This is the pronounced bond-strengthening effect that accompanies the accumulation of fluorines on the same carbon. Dolbier, W. R., Jr.; Medinger, K. S.; Greenberg, A.; Liebman, J. F. Tetrahedron 1982, 38, 2415. Dill, J. D.; Schleyer, P. V. R.; Pople, J. A. J. Am. Chem. Soc. 1976, 98, 1663.
11. Doyle, A. M.; Patrick, C. R.; Pedlar, A. E. J. Electroanal. Chem. 1971, 33, 23–30.
12. Hammett, L. P. Physical Organic Chemistry, 2nd ed.; McGraw-Hill: New York, 1970; pp 91–93.