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A model route to a brominated hydroxy[2,3-c]pyran- a potential precursor to extended quinones /Mei, Mawonga Newton. January 2008 (has links)
Thesis (MTech (Chemistry))--Cape Peninsula University of Technology, 2008. / Includes bibliographical references (leaves 77-79). Also available online.
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A model route to a brominated hydroxy[2,3-c]pyran- a potential precursor to extended quinonesMei, Mawonga N. January 2008 (has links)
A thesis submitted in fulfilment of the requirements for the degree Magister Technologiae
(Chemistry) in the Faculty of Applied Sciences, Department of Chemistry, Cape Peninsula
University of Technology, 2008 / Green et al. attempted to synthesize linear naphthopyranquinones from a naphthyl dioxolane
using a TiCl4 as a catalyst. They managed to synthesise an angular naphthopyran as well as
a linear naphthopyran in low yield. They showed that reducing the steric strain at position 1
of the naphthyl dioxolane afforded a low percentage yield of the linear naphthopyran plus an
angular one.
This thesis describes the synthesis of linear naphthopyrans with an improved percentage
yield using TiCl4 as a catalyst. This was achieved by placing a OMe group of less steric
hinderance at position 1 and a Br atom at position 4 of a naphthyl dioxolane. The OMe group
at position 1 was to allow isomerisation to occur at position 2, and the Br atom was to inhibit
isomerisation at position 4, thereby inhibiting the formation of the angular naphthopyran.
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