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Date of Award

1977

Document Type

Dissertation

Degree Name

Doctor of Philosophy (Ph.D.)

Department

Graduate School

First Advisor

Paul H. Gross

First Committee Member

Charles A. Matuszak

Second Committee Member

Herschel Frye

Third Committee Member

Michael Minch

Fourth Committee Member

David Fries

Abstract

The decision to attempt the synthesis of furo [3, 2-b] furan was based on four considerations. Firstly, there are an abundance of synthetic and naturally occurring compounds, especially carbohydrate derivatives, containing this ring system in a partially or fully saturated state. Secondly, some of these compounds are physiologically active and others are important industrially. Thirdly, no compound, synthetic or naturally occuring, containing the fully unsaturated nucleus has been reported. Yet this molecule has an uninterrupted chain of six carbon atoms and may conceivably be formed from certain hexose derivatives. By analogy with compounds containing the saturated ring, furo[3,2-b] furan may be physiologically active. Lastly, there is only one synthetic 3-alkoxyfuran, 3·-methoxyfuran. Any intermediate successes toward the stated goal as well as achievement of the final objective will expand knowledge in the difficult area of 3-substituted furan synthesis especially in the presently unexamined area of 3-alkoxyfuran synthesis.

Pages

143

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