Some applications of sulphur inorganic synthesis
Some applications of sulphur inorganic synthesis
The development of new synthetic methods in organic chemistry is of importance because new routes to total syntheses are thereby revealed. Chapter One deals with the reactions of oximes with benzenesulphenyl chloride, in an attempt to transpose a carbonyl group. A new reaction was discovered, leading to the synthesis of substituted enamides. A range of allene sulphoxides have been prepared, and their reactions studied. P255 in methylene chloride reduced the allenyl sulphoxides to the synthetically useful allenyl sulphides, as illustrated by the synthesis of the natural products a -atlantone and acetyldipentene. Introduction ofa methoxy group into the benzene ring was found to facilitate hydrolysis of the allenyl sulphides.Chapter Three is concerned with the chemistry of olefinic sulphides. Metallation of phenyl vinyl sulphide has been studied, and applied to the synthesis of various five membered rings, including dihydrojasmone and a prostaglandin precursor. A novel unsaturated ketone synthesis is described, which relies on the acid catalysed double bond shift in 2phenylthio allylic and allenic alcohols. The interaction between olefinic sulphides and iminium salts is described, and finally further applications of the Claisen rearrangement in organo sulphur chemistry has been investigated.
University of Southampton
1978
Parsons, Phillip James
(1978)
Some applications of sulphur inorganic synthesis.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The development of new synthetic methods in organic chemistry is of importance because new routes to total syntheses are thereby revealed. Chapter One deals with the reactions of oximes with benzenesulphenyl chloride, in an attempt to transpose a carbonyl group. A new reaction was discovered, leading to the synthesis of substituted enamides. A range of allene sulphoxides have been prepared, and their reactions studied. P255 in methylene chloride reduced the allenyl sulphoxides to the synthetically useful allenyl sulphides, as illustrated by the synthesis of the natural products a -atlantone and acetyldipentene. Introduction ofa methoxy group into the benzene ring was found to facilitate hydrolysis of the allenyl sulphides.Chapter Three is concerned with the chemistry of olefinic sulphides. Metallation of phenyl vinyl sulphide has been studied, and applied to the synthesis of various five membered rings, including dihydrojasmone and a prostaglandin precursor. A novel unsaturated ketone synthesis is described, which relies on the acid catalysed double bond shift in 2phenylthio allylic and allenic alcohols. The interaction between olefinic sulphides and iminium salts is described, and finally further applications of the Claisen rearrangement in organo sulphur chemistry has been investigated.
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Published date: 1978
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Local EPrints ID: 458406
URI: http://eprints.soton.ac.uk/id/eprint/458406
PURE UUID: 42a70ef1-5c79-44f9-b821-3a242a5cbb20
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Date deposited: 04 Jul 2022 16:48
Last modified: 04 Jul 2022 16:48
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Author:
Phillip James Parsons
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