The literature on preparation and oxidation of carbanions is reviewed. Attempted preparation of many new carbanions, using Lochmann's base (potassium t-butoxide/n-butyllithium), is described; dianions 59, 76, and 85 were prepared for the first time. Preparation of 85, calculated to have the least delocalization energy of all six-carbon acyclic carbanions, completes the series of six-carbon acyclic dianions. Reaction of these and three other dicarbanions (o-48, m-58, and p-58) with dihalides and oxidizing agents were investigated. The shortest routes to certain {n}- and {n,n}-cyclophanes resulted. Good yields were obtained of {9}- and -metacyclophane. Several {n}-2,6-pyridinophanes were synthesized from dianion 59. {6,6}- and {7,7}-metacyclophane and {5,5}-, {7,7}-, and {9,9}- orthocyclophane were synthesized for the first time.
| Identifer | oai:union.ndltd.org:arizona.edu/oai:arizona.openrepository.com:10150/187736 |
| Date | January 1982 |
| Creators | OGLE, CRAIG ALAN. |
| Publisher | The University of Arizona. |
| Source Sets | University of Arizona |
| Language | English |
| Detected Language | English |
| Type | text, Dissertation-Reproduction (electronic) |
| Rights | Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. |
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