Date of Award

1999

Degree Type

Dissertation

Degree Name

Ph.D.

Department

Chemistry and Biochemistry

First Advisor

Green, J.

Keywords

Chemistry, Organic.

Rights

CC BY-NC-ND 4.0

Abstract

Chapter 1. The nucleophilic addition of alkyl and arylmetals to 1 was examined. When the reaction was mediated by Ti(O iPr)4, diastereomeric excesses ranged from 77% to >94%. X-ray crystallography suggested that the major diastereomer had the absolute configuration of S. Conjugate addition of alkylmetal nucleophiles was attempted on 2 and 3 without success. Chapter 2. The preparation of meta-disubstituted arenechromium tricarbonyl complexes was attempted. The initial phase of this research involved the directed ortho lithiation of 4, with thioether directing groups. In the case of the 4, carrying out the reaction in Et 20 led to the metallation in the ortho' position. In THF lithiation occurred in both the meta and ortho' position. Desulfurization was attempted on the unsubstituted thiophenyl complex 4. The use of both Raney Nickel and Nickel Boride led to the formation of the desulfurized complex and its decomplexed analogue in equal proportions. Chapter 3. A series of chromium tricarbonyl complexes with benzylic and non-benzylic alcohol functionalities were subjected to DMSO-TFAA and DMSO/SO3-pyridine. Yields of carbonyl complexes ranged from 61--80% for the DMSO-TFAA oxidation and from 60--81% for the DMSO/SO 3-pyridine oxidation. Source: Dissertation Abstracts International, Volume: 61-09, Section: B, page: 4728. Adviser: James Richard Green. Thesis (Ph.D.)--University of Windsor (Canada), 1999.

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