Chemistry and Chemical Biology ETDs

Gene Sumrell

Publication Date

5-20-1948

Abstract

It was decided in this problem to prepare 2-phenyl-2,1,3-triazole-4-carboxaldehyde (III) as a starting material by the method suggested by Hann and Hudson and run a number of typical aldehyde reactions with it. The preparation of (III) involved: (1) The hydrolysis of sucrose to form glucose and fructose; (2) conversion of these two sugars to D-glucose phenylosazone (I), by reaction with phenylhydrazine; (3) transformation of (I) to D-glucose phenylosotraizole (II), by the action of hot aqueous copper sulfate; and (4) oxidation of the side chain from (II) with sodium periodate, forming (III).

The reactions selected were: (1) the Grignard reaction; (2) the Perkin reaction; (3) condensation of the aldehyde with a diamine to yield an imidazolidine; (4) oxidation to the acid and condensation of this acid with a diamine to yield an imidazoline; (5) condensation with acetone; and (6) a crossed Cannizzaro reaction, yielding primarily 2-phenyl-2,1,3-triazol-4-yl-carbinol.

Project Sponsors

Lilly Research Laboratories

Language

English

Document Type

Thesis

Degree Name

Chemistry

Level of Degree

Masters

Department Name

Department of Chemistry and Chemical Biology

First Committee Member (Chair)

Jesse LeRoy Riebsomer

Second Committee Member

John Francis Suttle

Third Committee Member

William Jacob Koster

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