Linda Hobart

Abstract

Synthesis of methyl substituted phenols (via various diazonium salts), to be used as a monomer in the synthesis of ordered polyesters and to study the liquid crystal continuum from monomer-to-oligomer-to-polymer, was attempted. Deblocking of di(methoxyphenyl) terephthalates with sodium ethanethiolate in dimethylformamide resulted in the preferential cleavage of the ester linkage over the alkyl -aromatic ether linkage. A number of cleavage products resulted, depending upon the reaction conditions. 4,4'[sulfonyl bis(ρ-phenylene ether)] dianisole was prepared as a model compound to be used in the ordered poly(ester-sulfone) study. Deblocking with hydrobromic and hydrobromic acid-acetic acid cosolvents was successful. However, deblocking wtih sodium ethanethiolate in dimethylformamide resulted in preferential cleavage of the aryl-aryl ether linkage over the alkyl-aromatic ether linkage. Attempts to synthesize 4,4'-[sulfonyl bis(p-phenylene ether)] dianisole by the Ullmann sythesis of diaryl ethers was unsuccessful. The effect of para-substituents on aromatic-nucleophic substitution reactions, in cleavage reactions of diaryl ethers by sodium ethanethiolate in diamethylformamide, was studied. Electron-withdrawing groups were found to facilitate the cleavage reaction.

Library of Congress Subject Headings

Polyesters; Sulfones; Ethers; Carbon compounds; Chemical reactions

Publication Date

6-1-1985

Document Type

Thesis

Department, Program, or Center

School of Chemistry and Materials Science (COS)

Advisor

Not listed

Comments

Note: imported from RIT’s Digital Media Library running on DSpace to RIT Scholar Works in December 2013.

Physical copy available from RIT's Wallace Library at TP1180.P6 H6 1985

Campus

RIT – Main Campus

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