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

PDF

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

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