Abstract
The title 1,3-dibromo- l, l-difluoro compounds are dehydrobrominated in the presence of l,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Reaction of simple saturated dibromides with DBU at 25 °C affords moderate yields of monoelimination products in which the reaction is 100% stereoselective and regioselective. Highly conjugated dienes are synthesized at mild reaction conditions in contrast to simple alkyl or pentafluorophenyl dienes which are inaccessible via a double dehydrobromination reaction due to the unexpected formation of trifluoromethyl compounds. Aromatic gem-difluorodienes react with 4-phenyl-1,2,4-triazoline-3,5-dione and a mechanistic experiment demonstrates the relative reactivities of the isomers of 1, l-difluoro-4-phenyl-1,3-butadiene in a Diels-Alder reaction. The unfluorinated analogue of 1, l-difluoro-4-phenyl-1,3-butadiene reacts completely and rapidly with maleic anhydride while 1,1-dilluoro-4-phenyl-1,3-butadiene remains inert towards this classical dienophile.
Notes
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Graduation Date
1991
Semester
Spring
Advisor
Elsheimer, Seth
Degree
Master of Science (M.S.)
College
College of Arts and Sciences
Department
Chemistry
Format
Pages
111 p.
Language
English
Length of Campus-only Access
None
Access Status
Masters Thesis (Open Access)
Identifier
DP0028084
Subjects
Arts and Sciences -- Dissertations, Academic; Dissertations, Academic -- Arts and Sciences
STARS Citation
Foti, Christopher, "Dehydrobromination of some 1,3-dibromo-1,1- difluoro compounds som (4+2) cycloaddition reactions of 1,1-difluoro-1,3-dienes" (1991). Retrospective Theses and Dissertations. 3831.
https://stars.library.ucf.edu/rtd/3831
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