The title compound was synthesized and its chemistry studied for the first time. It reacts with carbon electrophiles initially at its $ epsilon$-position. The condensation with aliphatic imidazolides or similar acylating agents furnished methyl 6-alkyl-2,4-dihydroxy benzoates in a 5C + 1C fashion. Reaction with aromatic imidazolides, also in a 5C + 1C manner, gave unsymmetrical biphenyls with the 2-carbomethoxy-3,5-dihydroxyphenyl moiety. A regiocontrolled synthesis of naphthalene derivatives was developed by reaction with the appropriate 1,3,5-tris-electrophiles in a 5C + 5C fashion.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.75352 |
| Date | January 1987 |
| Creators | Stössel, Daniel. |
| 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: 000417618, proquestno: AAINL38219, Theses scanned by UMI/ProQuest. |
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