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The Jocic reaction and the synthesis of Vitamin E
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Tomlinson, James M. (2018) The Jocic reaction and the synthesis of Vitamin E. PhD thesis, University of Warwick.
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Official URL: http://webcat.warwick.ac.uk/record=b3231781~S15
Abstract
This thesis begins with an introduction to Vitamin E and the Jocic reaction. Chapter 1 provides a review of the biological activity of vitamin E and related compounds and the synthesis, both racemic and asymmetric, of vitamin E compounds. Also discussed in this chapter is the Jocic reaction and the synthesis of trichloromethyl alcohol compounds.
Chapter 2 describes the asymmetric total syntheses of both α- and β-tocopherol, where an intramolecular Jocic reaction was used to provide a high enantiomeric excess. Difficulties encountered during the synthesis, and how these were overcome, are detailed.
Chapter 3 describes the novel use of hydride as a nucleophile in the Jocic reaction with tertiary polychloromethyl alcohols. This one-carbon homologation procedure was improved by the use of dichloro- rather than trichloromethyl alcohols. The scope of the reaction, mechanisms and stereochemical implications are discussed.
Item Type: | Thesis (PhD) | ||||
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Subjects: | Q Science > QD Chemistry Q Science > QP Physiology |
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Library of Congress Subject Headings (LCSH): | Vitamin E, Asymmetric synthesis, Chemical reactions, Stereochemistry | ||||
Official Date: | April 2018 | ||||
Dates: |
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Institution: | University of Warwick | ||||
Theses Department: | Department of Chemistry | ||||
Thesis Type: | PhD | ||||
Publication Status: | Unpublished | ||||
Supervisor(s)/Advisor: | Fox, David J. (David John) | ||||
Sponsors: | University of Warwick | ||||
Extent: | 323 leaves : illustrations | ||||
Language: | eng |
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