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A model route to a brominated hydroxy[2,3-c]pyran- a potential precursor to extended quinones

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.

Identiferoai:union.ndltd.org:netd.ac.za/oai:union.ndltd.org:cput/oai:localhost:20.500.11838/749
Date January 2008
CreatorsMei, Mawonga N.
ContributorsHugo, V., Prof
PublisherCape Peninsula University of Technology
Source SetsSouth African National ETD Portal
LanguageEnglish
Detected LanguageEnglish
TypeThesis
Rightshttp://creativecommons.org/licenses/by-nc-sa/3.0/za/

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