Base promoted rearrangement of quaternary ammonium salts derived from 2-aryl-3-(n,n-dimethylamino)-1-propenes
Abstract
A variety of quaternary ammonium salts derived from 2-aryl-3-(N,N-dimethylamino)-1-propenes were treated with sodium hydride, abstraction of generating a nitrogen ylide through an acidic proton. The subsequent intramolecular rearrangement took place by either a [2,3] sigmatropic rearrangement or the [ 1 , 2 ] Stevens rearrangement. The rearranged product was produced cleanly and in good yield when the functionality alpha to the acidic proton was an ester group, a substituted benzoyl group, or a ni tro-substi tuted phenyl group. The rearrangement did not occur under rearrangement conditions when this functionality was the phenyl group or a phenyl ring substituted with an electron-releasing group. The reaction to the rearranged product provided efficient access to unique and highly functionalized a-amino acid derivatives.
Notes
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Graduation Date
1991
Semester
Summer
Advisor
Gupton, John T.
Degree
Master of Science (M.S.)
College
College of Arts and Sciences
Department
Chemistry
Format
Pages
171 p.
Language
English
Length of Campus-only Access
None
Access Status
Masters Thesis (Open Access)
Identifier
DP0027970
Subjects
Arts and Sciences -- Dissertations, Academic; Dissertations, Academic -- Arts and Sciences
STARS Citation
Birnstihl, Jennifer Maurine, "Base promoted rearrangement of quaternary ammonium salts derived from 2-aryl-3-(n,n-dimethylamino)-1-propenes" (1991). Retrospective Theses and Dissertations. 3792.
https://stars.library.ucf.edu/rtd/3792