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.
| Identifer | oai:union.ndltd.org:BGMYU2/oai:scholarsarchive.byu.edu:etd-9188 |
| Date | 01 May 1972 |
| Creators | Chen, Edward Ying-shih |
| Publisher | BYU ScholarsArchive |
| Source Sets | Brigham Young University |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | Theses and Dissertations |
| Rights | http://lib.byu.edu/about/copyright/ |
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