Thesis advisor: James P. Morken / Described herein is the exploration of a novel methodology whereby boronate-ester bearing cyclopentanes are produced by reaction between an unactivated olefin and what is described as a boron alkylidene. The mechanism is evaluated and concluded to proceed through a boracyclic intermediate that is achieved by a closed-shell, carbanion addition to the olefin. This mechanistic conclusion is arrived upon by considering two likely alternative routes (an open-shell, radical cyclization and a [2+2] concerted process) and providing evidence to refute them. A reaction scope is established as well as the utility of the methodology through the racemic synthesis of a natural sesquiterpene: aphanamal. Finally, the future of the reaction development will be considered by providing a single example of a 6-endo cyclization. / Thesis (MS) — Boston College, 2017. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.
| Identifer | oai:union.ndltd.org:BOSTON/oai:dlib.bc.edu:bc-ir_107597 |
| Date | January 2017 |
| Creators | Deaton, Timothy Maxwell |
| Publisher | Boston College |
| Source Sets | Boston College |
| Language | English |
| Detected Language | English |
| Type | Text, thesis |
| Format | electronic, application/pdf |
| Rights | Copyright is held by the author, with all rights reserved, unless otherwise noted. |
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