Abstract

The reaction of monohalonaphthalenes with metal alkoxides and mercaptides in a solvent mixture of the corresponding alcohol and dimethyl sulfoxide (DMSO) has been studied. These reactions are convenient methods for the preparation of alkylnaphthyl ethers and sulfides. Only direct nucleophilic substitution was observed in the reactions of bromonaphthalenes with sodium methoxide and sodium nbutyl mercaptide. The reaction of fluoronaphthalene with potassium t-butoxide also proceeded by way of direct nucleophilic substitution rather than the 1,2-dehydronaphthalene intermediate as in the reactions of bromonaphthalene with potassium t-butoxide. The use of a base which is weaker than t-butoxide can change the apparent reaction mechanism from the dehydronaphthalene to direct nucleophilic substitution.

Degree

MS

College and Department

Chemistry and Biochemistry

Rights

http://lib.byu.edu/about/copyright/

Date Submitted

1972-05-01

Document Type

Thesis

Handle

http://hdl.lib.byu.edu/1877/Letd535

Keywords

Ether, Sulfides

Language

English

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