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A thiyl radical mediated cascade sequence for the co-cyclisation of 1,6-hexadienes with sulfur atom transfer

A thiyl radical mediated cascade sequence for the co-cyclisation of 1,6-hexadienes with sulfur atom transfer
A thiyl radical mediated cascade sequence for the co-cyclisation of 1,6-hexadienes with sulfur atom transfer
The paper describes a method for effecting the co-cyclisation of 1,6-dienes with concomitant sulfur atom transfer. The key step is a cascade reaction involving the addition of a thiyl radical to an alkene, cyclisation through a chair-like transition state and termination by homolytic substitution at sulfur. It has been used to synthesise a broad range of fused thiabicyclo[3.3.0]octanes.
cyclisations, photochemistry, radicals and radical reactions, sulfur heterocycleshomolytic substitution, cyclization reactions, condensed thiophenes, lactam synthesis, disulfide, dienylamides, system
0040-4039
9345-9349
Harrowven, D. C.
1c293b83-4291-4301-a7a4-167d6a146d01
Hannam, J. C.
225e6464-69bd-480a-ba0b-9ad9fbb85bef
Lucas, M. C.
7c5c896a-fdb1-4a54-b5dd-545f0a20392b
Newman, N. A.
d8631f73-4cbd-46ad-b2ea-da254ff8a79f
Howes, P. D.
23bd5ae7-2e44-47df-96be-51c8c4eee95f
Harrowven, D. C.
1c293b83-4291-4301-a7a4-167d6a146d01
Hannam, J. C.
225e6464-69bd-480a-ba0b-9ad9fbb85bef
Lucas, M. C.
7c5c896a-fdb1-4a54-b5dd-545f0a20392b
Newman, N. A.
d8631f73-4cbd-46ad-b2ea-da254ff8a79f
Howes, P. D.
23bd5ae7-2e44-47df-96be-51c8c4eee95f

Harrowven, D. C., Hannam, J. C., Lucas, M. C., Newman, N. A. and Howes, P. D. (2000) A thiyl radical mediated cascade sequence for the co-cyclisation of 1,6-hexadienes with sulfur atom transfer. Tetrahedron Letters, 41 (48), 9345-9349. (doi:10.1016/S0040-4039(00)01701-9).

Record type: Article

Abstract

The paper describes a method for effecting the co-cyclisation of 1,6-dienes with concomitant sulfur atom transfer. The key step is a cascade reaction involving the addition of a thiyl radical to an alkene, cyclisation through a chair-like transition state and termination by homolytic substitution at sulfur. It has been used to synthesise a broad range of fused thiabicyclo[3.3.0]octanes.

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More information

Published date: 25 November 2000
Keywords: cyclisations, photochemistry, radicals and radical reactions, sulfur heterocycleshomolytic substitution, cyclization reactions, condensed thiophenes, lactam synthesis, disulfide, dienylamides, system

Identifiers

Local EPrints ID: 18853
URI: http://eprints.soton.ac.uk/id/eprint/18853
ISSN: 0040-4039
PURE UUID: 9de3f847-1231-4652-9587-51106783cd87

Catalogue record

Date deposited: 15 Dec 2005
Last modified: 15 Jul 2019 19:28

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