Sulfur chemistry on the solid phase
Sulfur chemistry on the solid phase
This thesis is concerned with the chemistry of thioesters immobilised on solid supports, and radical cyclisations of solid-supported 1,6-dienes using sulfur-centred radicals.
A new method for linking substrates to a solid support using a thioester linkage is described, in which a thioamide is reacted with either Merrifield resin or a brominated Wang linker on a polystyrene bead, in the presence of aqueous DMF and sodium iodide. New methods for cleaving substrates linked to a solid support through a thioester linker are discussed, leading to tertiary alcohols, ketones and lactones, all in good yield.
The cyclisation of a range of 1,6-dienes using phenylthiyl radicals is described, both for resin-bound substrates and those in solution. The 1,6-dienes are immobilised on solid-support using a malonate linker. The diastereoselectivity of the cyclisation reaction is also reported.
Radical cyclisations of the aforementioned 1,6-dienes using p-tolyl benzeneselenosulfonate are also described, for both resin-bound substrates and those in solution. The diastereoselectivity of the cyclisation reaction is also reported.
University of Southampton
May, Peter J
c827488c-5dcc-444d-b712-2f1680e86dd8
2002
May, Peter J
c827488c-5dcc-444d-b712-2f1680e86dd8
May, Peter J
(2002)
Sulfur chemistry on the solid phase.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
This thesis is concerned with the chemistry of thioesters immobilised on solid supports, and radical cyclisations of solid-supported 1,6-dienes using sulfur-centred radicals.
A new method for linking substrates to a solid support using a thioester linkage is described, in which a thioamide is reacted with either Merrifield resin or a brominated Wang linker on a polystyrene bead, in the presence of aqueous DMF and sodium iodide. New methods for cleaving substrates linked to a solid support through a thioester linker are discussed, leading to tertiary alcohols, ketones and lactones, all in good yield.
The cyclisation of a range of 1,6-dienes using phenylthiyl radicals is described, both for resin-bound substrates and those in solution. The 1,6-dienes are immobilised on solid-support using a malonate linker. The diastereoselectivity of the cyclisation reaction is also reported.
Radical cyclisations of the aforementioned 1,6-dienes using p-tolyl benzeneselenosulfonate are also described, for both resin-bound substrates and those in solution. The diastereoselectivity of the cyclisation reaction is also reported.
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Published date: 2002
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Local EPrints ID: 464716
URI: http://eprints.soton.ac.uk/id/eprint/464716
PURE UUID: 8ae55af2-8004-4e09-a0af-26f5c061e939
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Date deposited: 04 Jul 2022 23:58
Last modified: 16 Mar 2024 19:43
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Author:
Peter J May
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