Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 185, Issue -, Pages 213-223Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2015.09.016
Keywords
Photocyclization; Perfluoro-cis-1,2-dimethyl-butadienylbenzene; 1,2-Difluoro-3,4-bis(trifluoromethyl)naphthalene; Photoelimination of HF; 1,1,2-Trifluoro-3,4-bis(trifluoromethyl)-1,4-dihydronaphthalene
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Funding
- National Science Foundation
- Air Force Office of Scientific Research
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Photoirradiation of the titled compounds perfluoro-cis-1,2-dimethyl-butadienyl benzenes (1), which were prepared in several steps from perfluorovinyl bromide, results in the formation of the corresponding novel naphthalene derivatives and 1,4-dihydronaphthalenes. Isolated 1,1,2-trifluoro-3,4-bis(trifluoromethyl)-1,4-dihydronaphthalene (3a) could be converted into 1,2-bistrifluoromethy13,4-difluoronaphthalene (2a) by base treatment (DABCO); however, 3a did not lead to 2a by photoreaction, suggesting 3a was not a possible photochemical precursor. Competitive photoreaction studies suggest that varying the substituent on benzene ring (e.g. methyl or trifluoromethyl) does not significantly affect the reaction rate. Presently, this reaction mechanism is not yet clearly understood. (C) 2016 Published by Elsevier B.V.
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