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Synlett 1992; 1992(10): 823-824
DOI: 10.1055/s-1992-21505
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Synthesis of Bis-Crown Thioethers Containing a Common Aromatic Unit. Regioselectivity Based on the Length of the -S(CH2)nS(CH2)nS-Chain

Stephen J. Loeb* , George K. H. Shimizu
  • *Department of Chemistry and Biochemistry, University of Windsor, Windsor, Ontario N9B 3P4, Canada
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Publication Date:
08 March 2002 (online)

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The thioether macrocycles 2,5,8,17,20,23-hexathia-[9](1,3)[9](4,6)cyclophane and 2,6,10,19,23,27-hexathia[11](1,2) [11](4,5)cyclophane have been synthesized by a completely regioselective ring closure reaction. The reaction of one equivalent of 1,2,4,5-tetrakis(bromomethyl)benzene with 2 equivalents of 3-thiapentane-1,5-dithiol or 4-thiaheptane-1,7-dithiol in DMF in the presence of cesium carbonate yields the (1,3)(4,6), meta, and (1,2)(4,5), ortho, 1:2 cyclization products respectively.