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


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), pp. 9345-9349. (doi:10.1016/S0040-4039(00)01701-9).

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Description/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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/S0040-4039(00)01701-9
ISSNs: 0040-4039 (print)
Keywords: cyclisations, photochemistry, radicals and radical reactions, sulfur heterocycleshomolytic substitution, cyclization reactions, condensed thiophenes, lactam synthesis, disulfide, dienylamides, system
Subjects:
ePrint ID: 18853
Date :
Date Event
25 November 2000Published
Date Deposited: 15 Dec 2005
Last Modified: 16 Apr 2017 23:08
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/18853

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