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Synthesis 1994; 1994(10): 1067-1071
DOI: 10.1055/s-1994-25639
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Cycloaddition Reactions of [1,2]Dithiolo[1,2]dithiole Derivatives with Dimethyl Acetylenedicarboxylate: Formation of New Bi-, Tri- and Tetracyclic Thiopyran Derivatives

E. Fanghänel* , T. Palmer, J. Kersten, R. Ludwigs, K. Peters, H. G. Von Schnering
  • *Martin-Luther-Universität, Institut für Organische Chemie, D-06217 Merseburg, Germany
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Publication Date:
27 September 2002 (online)

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By cycloaddition reactions of the title compounds 1, new spiro[1,3-dithiole-thiopyran] derivatives 3 and 5 are available. Their cleavage with mercury(II) acetate leads to the corresponding bicyclic thiopyran-4-ones 9 and 10. Starting from 3H,6H-[1,2]dithiolo[4,3-c][1,2]dithiole- 3,6-dithione (1d), besides 4H,8H-2,3,6,7,4′,5′,4″,5″- octa-(methoxycarbonyl)thiopyrano[3,2-b]thiopyran-4-spiro-2′-(1′,3′- dithiole)-8-spiro-2″-(1″,3″-dithiole) (5), the tetra(5′,6′- methoxycarbonyl-1′,4′-dithiino)[2,3-c][2,3-e][2,3-i] [2,3-k]-1,2,7,8-tetrathiacyclododeca-3,5,9,11-tetraene (8) is formed.

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