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

PDF

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

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