Mechanisms for the alkaline hydrolysis of dibromodifluoromethane-alkene adducts to a,B-unsaturated carboxylates
Keywords
Carboxylic acids, Hydrolysis
Abstract
Alternative mechanisms for the title reactions are probed. The previously reported pathway involving double dehydrobromination to a difluorodiene is operative in at least one case, but this route is specifically excluded for systems that can not dehydrobrominate to dienes yet yield carboxylates upon alkaline hydrolysis. Although SN2, SN1, SRN1, and monoelimination-addition processes appear possible, an SN2' mechanism is implicated by studies on model compounds. Bromodifluoromethyl groups attached to quaternary carbons are unreactive toward alkaline hydrolysis.
Notes
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Graduation Date
1999
Semester
Spring
Advisor
Elsheimer, Seth R.
Degree
Master of Science (M.S.)
College
College of Arts and Sciences
Department
Chemistry
Format
Pages
44 p.
Language
English
Length of Campus-only Access
None
Access Status
Masters Thesis (Open Access)
Identifier
DP0028705
Subjects
Arts and Sciences -- Dissertations, Academic; Dissertations, Academic -- Arts and Sciences
STARS Citation
Swanson, JoAnne Ligeri, "Mechanisms for the alkaline hydrolysis of dibromodifluoromethane-alkene adducts to a,B-unsaturated carboxylates" (1999). Retrospective Theses and Dissertations. 2267.
https://stars.library.ucf.edu/rtd/2267