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Synlett 1994; 1994(3): 201-203
DOI: 10.1055/s-1994-22794
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The Chemistry of 1,2-Dithiins: Synthesis of 1,2-Dithiin and 3,6-Disubstituted 1,2-Dithiins

Masato Koreeda* , Wu Yang
  • *Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109-1055, USA
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Publication Date:
22 March 2002 (online)

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An efficient, generally applicable method for the synthesis of a variety of 3,6-disubstituted 1,2-dithiins has been established. The method involves the regio- and stereoselective 1,4-bis-addition of alkylthiols to 1,4-disubstituted 1,3-butadiyne at room temperature in DMF in the presence of a catalytic amount of KOH. Subsequent reductive removal of the thiol-protecting group with Li/liq NH3/THF at -78 °C followed by oxidative ring closure of the resulting dilithium dithioenolates with I2/KI provides the red-colored 1,2-dithiins.