Nucleophilic displacement in polyhalogenoaromatic compounds. Part 8. Kinetics of methoxydefluorination of some polyfluoronaphthalenes
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 746-750
- https://doi.org/10.1039/p29780000746
Abstract
The kinetics of methoxydefluorination of some 2-X-heptafluoronaphthalenes (X = H, F, Cl, OMe, or C6H5) and of 1,2,3,4,5,6-hexafluoronaphthalene in methanol at 323.2 K have been measured. The orientation of attack has been confirmed in the naphthalene derivatives as mainly involving displacement at C-6, although some evidence has been found for attack at C-7 in 2-methoxyheptafluoronaphthalene. Similar studies have been made of the orientation of methoxydefluorination of 2,3,4,5,6-penta- and of octa-fluorotoluene, together with a study of the rate of reaction of the latter compound. The rate constants are explained in terms of a transmission of the total substituent effect of the groups across the biannular system.Keywords
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