Tomlinson, James M. (2018) The Jocic reaction and the synthesis of Vitamin E. PhD thesis, University of Warwick.

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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 or Dissertation (PhD)
Subjects:	Q Science > QD Chemistry Q Science > QP Physiology
Library of Congress Subject Headings (LCSH):	Vitamin E, Asymmetric synthesis, Chemical reactions, Stereochemistry
Official Date:	April 2018
Dates:	Date Event April 2018 UNSPECIFIED
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Publication Status:	Unpublished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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