This report discusses research involving the preparation of germinal difluorodienes. Free radical addition of dibromodifluoromethane to 1-hexene and cyclohexene was performed, followed by a double dehydrohalogenation to yield 1,1-difluoro-1,3-heptadiene and 3-(difluoromethylene)cyclohexene, respectively. NMR, IR, and mass spectral data were obtained and presented as groundwork for further research. A study comparing the free radical initiators, benzoyl peroxide and 2,2’-azobis-(2-methyl)proprionitrile (AIBN) was included, showing neither as ideal initiators for the free radical additions performed. The relative stabilities of the bromodifluoromethyl and the difluoroiodomethyl radicals were approximated. A Diels-Alder reaction of 1,1-difluoro-1,3-heptadiene with 4-phenyl-1,2,4-triazoline-3,5-dione produced the expected [4 + 2] cycloadduct in good yield.
| Identifer | oai:union.ndltd.org:ucf.edu/oai:stars.library.ucf.edu:rtd-6048 |
| Date | 01 January 1987 |
| Creators | Landavazo, Antonio |
| Publisher | University of Central Florida |
| Source Sets | University of Central Florida |
| Language | English |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | Retrospective Theses and Dissertations |
| Rights | Public Domain |
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