9,12-Dithia-trans-bicyclo[6.4.0]dodeca-2,4,6,10-tetraene system, an example of a trans-fused cyclo-octa-1,3,5-triene

Abstract

Reaction of the 1,2-dithiols (1a–c) with cyclo-octatetraene trans-dihalides led to dérivatives (3a–c) of the title system, whose special steric features permit synthetically useful transformations; thus thermal rearrangement gave the 3,4-fused 1,4-dithiinocyclo-octa-1,3,5-triene (4), base-induced isomerisation gave the 1,4-dithia[12]annulene (8), BF₃-catalysed rearrangement gave the 2-benzyl-1,3-dithiole (11), and dehydrogenation gave the 1,4-dithiinocyclo-octatetraene (12).