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Paper | Special issue | Vol 84, No. 2, 2012, pp.1113-1122
Published online, 13th September, 2011
DOI: 10.3987/COM-11-S(P)93
Synthesis of Norbornane-Fused 1,3-Dithiolanes and Evaluation of 1,3-Dithiolane-Containing Polymers as Absorbants for Mercury(II) Salts

R. Alan Aitken,* Kati M. Aitken, Stuart Lambert, Richard Playfair, and Neil J. Wilson

*School of Chemistry, University of St. Andrews, Fife KY 16 9ST, U.K.


Hydrolysis of the zwitterionic adducts formed from Bu3P, CS2 and norbornene or norbornadiene gives Bu3PO and the corresponding norbornane-fused 1,3-dithiolanes. Oxidation of these gives endo-sulfoxides while attempted hydrolysis using HgCl2 and CdCO3 instead leads to formation of crystalline 1:1 HgCl2 adducts. Based on this observation, a range of robust and readily accessible polymers containing norbornane-fused dithiolane units are evaluated for absorption of HgCl2 from aqueous solution.