Date of Award

Spring 1982

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry & Biochemistry

Program/Concentration

Chemistry

Committee Director

Frank E. Scully, Jr.

Committee Member

Charles E. Bell

Committee Member

Roy L. Williams

Committee Member

Billy T. Upchurch

Call Number for Print

Special Collections LD4331.C45 T63

Abstract

The compounds: 3-allylpiperidine, 3-ethylpiperidine and 3-n-butylpiperidine have been synthesized by regioselectively alkylating the three position of piperidine. Piperidine was converted to N-chloropiperidine and then dehydrohalogenated to produce Δ1-piperideine. The enamide anion was generated by adding solutions of Δ1-piperideine to ethylmagnesium bromide or lithium diisopropylamide. Addition of alkylhalides produced 3-alkyl- Δ1-piperideine which could be reduced or alkyllithiated to give 3-alkylpiperidines or 2,3-dialkylpiperidines respectively.

The yields of products were low and the reaction generated a continuum of mono- and di-alkylpiperidines and there was evidence that several dimeric piperideines were formed. The low yields were discussed in terms of the instability of the piperideine molecule and a strained transition state for generating the enamide anion.

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DOI

10.25777/cy5j-j882

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