Masters Theses

Date of Award

8-1997

Degree Type

Thesis

Degree Name

Master of Science

Major

Chemistry

Major Professor

Donald C Kleinfelter

Abstract

Spectroscopic properties of l-phenyI-4,4,5-trimethyl-5-hydroxy-6-oxa-7,7-diphenyl-lhydrindene- 2-one and some of its derivatives were studied using high resolution nuclear magnetic spectroscopy. The aryl groups present were the phenyl, ο-anisyl, ο-tolyl, and ο-ethylphenyl.

The ο-anisyl analog demonstrated restricted rotation on the NMR time scale through the appearance of two absorption positions for the ο-substituent protons. The acid-catalyzed dehydration product of the ο-anisyl compound also showed restricted rotation. However, the lithium aluminum hydride reduction product of the ο-anisyl analog did not have restricted rotation since the six-membered ring was cleaved during the reduction process.

The ο-tolyl analog showed an epimeric mixture. The acid-catalyzed dehydration product of this mixture, however, was not a mixture since the OH on the six-membered ring is absent. In addition, the ο-tolyl analog mixture was found theoretically to give four sodium borohydride reduction products. It also gave two lithium aluminum hydride reduction products since the six-membered ring was not retained.

The analysis of the ο-ethylphenyl analog showed one methyl absorption for the methyl portion of the ethyl group on the aryl ring. This indicated no restricted rotation had occurred for the system. In addition, NMR examination on the cyclic ketal of the phenyl oxidation product revealed that the methylene protons of the -OEt group were diastereotopic. The NMR spectrum of the two ο-anisyl diols, the ο-tolyl analog and derivatives, as well as the ο-ethylphenyl analog have been found to be different than previously reported.

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