Journal article
Unusual photocyclization of perfluoro cis-1,2-dimethyl-1,3-butadienyl benzenes as a means to synthesize partially fluorinated naphthalenes
Journal of fluorine chemistry, Vol.185, pp.213-223
05/01/2016
DOI: 10.1016/j.jfluchem.2015.09.016
Abstract
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.
Details
- Title: Subtitle
- Unusual photocyclization of perfluoro cis-1,2-dimethyl-1,3-butadienyl benzenes as a means to synthesize partially fluorinated naphthalenes
- Creators
- Michiharu Yamamoto - Univ Iowa, Dept Chem, Iowa City, IA 52242 USADale C. Swenson - University of IowaDonald J. Burton - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Journal of fluorine chemistry, Vol.185, pp.213-223
- DOI
- 10.1016/j.jfluchem.2015.09.016
- ISSN
- 0022-1139
- eISSN
- 1873-3328
- Publisher
- Elsevier
- Number of pages
- 11
- Grant note
- National Science Foundation; National Science Foundation (NSF) Air Force Office of Scientific Research; United States Department of Defense; Air Force Office of Scientific Research (AFOSR)
- Language
- English
- Date published
- 05/01/2016
- Academic Unit
- Chemistry
- Record Identifier
- 9984622048102771
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