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

Authors
Harrowven, DC Hannam, JC Lucas, MC Newman, NA Howes, PD
Citation
Dc. Harrowven et al., A thiyl radical mediated cascade sequence for the co-cyclisation of 1,6-hexadienes with sulfur atom transfer, TETRAHEDR L, 41(48), 2000, pp. 9345-9349
Citations number
34
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
48
Year of publication
2000
Pages
9345 - 9349
Database
ISI
SICI code
0040-4039(20001125)41:48<9345:ATRMCS>2.0.ZU;2-2
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. (C) 2000 Elsevier Science Ltd. All rights reserved.