Picture of UK Houses of Parliament

Leading national thinking on politics, government & public policy through Open Access research

Strathprints makes available scholarly Open Access content by researchers in the School of Government & Public Policy, based within the Faculty of Humanities & Social Sciences.

Research here is 1st in Scotland for research intensity and spans a wide range of domains. The Department of Politics demonstrates expertise in understanding parties, elections and public opinion, with additional emphases on political economy, institutions and international relations. This international angle is reflected in the European Policies Research Centre (EPRC) which conducts comparative research on public policy. Meanwhile, the Centre for Energy Policy provides independent expertise on energy, working across multidisciplinary groups to shape policy for a low carbon economy.

Explore the Open Access research of the School of Government & Public Policy. Or explore all of Strathclyde's Open Access research...

The acid-catalysed rearrangements of 4,5-bis(2-thienylhydroxymethyl)-1,3-dithiole-2-thione

Serebryakov, I.M. and Skabara, P.J. and Perepichka, I.F. (1999) The acid-catalysed rearrangements of 4,5-bis(2-thienylhydroxymethyl)-1,3-dithiole-2-thione. Journal of the Chemical Society, Perkin Transactions 2, 1999 (7). pp. 1405-1410. ISSN 1472-779X

Full text not available in this repository.Request a copy from the Strathclyde author

Abstract

Under strongly acidic conditions, the title compound 1 readily participates in several possible rearrangement pathways, affording a product distribution which is relative to the choice of solvent and acid catalyst. Thus, using chloroform or acetone as the solvents and HBr or HClO4 as the catalysts, compounds 2-4 have been isolated and fully characterised; in addition, compound 5 was identified in the reaction mixture and characterised by H-1 NMR spectroscopy. The reaction kinetics of the transformations have been studied by H-1 NMR spectroscopy, using deuterated chloroform or acetone as the NMR solvents. A key intermediate in the reaction mechanisms is the allylic carbocation 6, which rearranges to give the fused system 3; in the presence of bromide anions, the carbocation forms an ion-pair intermediate 7, leading to the formation of compounds 2, 4 and/or 5, depending on the solvent.