Base promoted rearrangement of quaternary ammonium salts derived from 2-aryl-3-(n,n-dimethylamino)-1-propenes
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.
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Gupton, John T.
Master of Science (M.S.)
College of Arts and Sciences
Length of Campus-only Access
Masters Thesis (Open Access)
Arts and Sciences -- Dissertations, Academic; Dissertations, Academic -- Arts and Sciences
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.