Abstract
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.
Graduation Date
1987
Semester
Fall
Advisor
Elsheimer, Seth Robert
Degree
Master of Science (M.S.)
College
College of Arts and Sciences
Department
Chemistry
Degree Program
Industrial Chemistry
Format
Pages
45 p.
Language
English
Rights
Public Domain
Length of Campus-only Access
None
Access Status
Masters Thesis (Open Access)
Identifier
DP0020552
STARS Citation
Landavazo, Antonio, "Preparation of Geminal Diflourodienes" (1987). Retrospective Theses and Dissertations. 5049.
https://stars.library.ucf.edu/rtd/5049