Date of Award

Spring 2002

Document Type

Thesis

Degree Name

Master of Science in Applied Chemistry - (M.S.)

Department

Chemical Engineering, Chemistry and Environmental Science

First Advisor

David S. Kristol

Second Advisor

Barbara B. Kebbekus

Third Advisor

Tamara M. Gund

Fourth Advisor

Louis Barash

Abstract

A one-step synthesis of the heterocycle 2-methyl-3,4,5-trichloropyrimidine by the cycloaddition of hexachloropropene with acetamidine hydrochloride in methanolic NaOH was attempted. The product was dark amber oil. A by-product of this reaction was sodium chloride. The proposed reaction was expected to proceed via a SN2 nucleophilic displacement of three chlorine atoms on hexachloropropene by acetamidine, the nucleophile. The proposed driving force for this transformation is the lone pair of electrons on the amidine nitrogen along with the electron withdrawing ability of three chlorines on hexachloropropene which induces a partial positive charge on the carbon. It is proposed that the chlorine atoms became good leaving groups based upon literature precedent presented in the introduction. The chlorine atoms act as good leaving groups via SN2 nucleophilic displacement by the nitrogen atoms. This thesis discusses a synthetic strategy for the possible synthesis of 2-methyl-3,4,5-trichloropyrimidine and its analogs.

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Chemistry Commons

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