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Sulfur chemistry on the solid phase

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
May, Peter J

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

Identifiers

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: 05 Jul 2022 03:00

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Author: Peter J May

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