Date of Award

1982

Degree Type

Thesis

Degree Name

Master of Science (MS)

Author's Department

Chemistry

First Advisor

David H. Buchanan

Abstract

Dibromotriphenylphosphorane (DTP) in acetonitrile at 50°C was found to cleave ß-naphthylmethyl phenyl ether in preference to ß-naphthyl benzyl ether, 62% and 30% cleavage, respectively. Reaction of ß-naphthyl benzyl ether in dichloromethane at reflux produced 67% cleavage.

The quasiphosphonium complexes obtained by reaction of phenolic compounds with DTP were found to be reduced by several reducing reagents to give the corresponding aromatic hydrocarbons. Reaction of p-cresol with DTP, followed by lithium aluminum hydride reduction gave 38% toluene; sodium naphthalide reduction in THF gave 32% toluene; sodium in liquid ammonia reduction gave 12% toluene; sodium naphthalide reduction in DMF gave 15% toluene. Reaction of ß-naphthol with DTP followed by lithium aluminum hydride reduction in THF gave no naphthalene.

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Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.

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