The reactions of 2,5-dimethoxytetrahydrofuran and 2,6-dimethoxytetrahydropyran with halotrimethylsilanes have unexpectedly given 1,4-dichloro-1,4-dimethoxybutane and 1,5-dihalo-1,5-dimethoxypentane, respectively. Some features of this reaction were investigated and a mechanism was proposed. / It was shown that 1,4-dichloro-1,4-dimethoxybutane was a mild reagent for the conversion of primary amine and amide to the corresponding N-alkyl and N-acyl pyrroles, respectively. As part of these applications, 2-(2-formylpyrrol-1-yl)-4-methylpentanoic acid, a compound isolated from flue-cured tobacco, was synthesized. / The use of acylpyrroles as active acylating agents was investigated. The preparation of (alpha)-substituted derivatives from ethyl 2-(1-pyrrolyl)acetate was achieved by using lithium hexamethyldisilazide as base. / As part of a synthetic study directed toward Nonactin, the bicyclic enol form 152 and keto form 153 were obtained by the reaction of 1-methoxyl-1,3-bis(Trimethylsiloxy)-1,3-pentadiene with 2,5-dimethoxytetrahydrofuran. The configurations at C-4 were determined with the aid of 200 MHz ('1)H nmr decoupled spectra. / A new rearrangement of (alpha)-acyloxy esters into 2-hydroxy-3-keto esters was observed.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.71909 |
| Date | January 1983 |
| Creators | Lee, Seung Dal. |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 000196477, proquestno: AAINK66651, Theses scanned by UMI/ProQuest. |
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