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A model route to a brominated hydroxy[2,3-c]pyran- a potential precursor to extended quinones
Author(s)
Mei, Mawonga N.
Date Issued
2008
Type
Thesis
Publisher
Cape Peninsula University of Technology
Abstract
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.
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.
Additional information
Thesis (MTech (Chemistry))--Cape Peninsula University of Technology, 2008
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