Reinecke, Manfred G.2019-10-112019-10-1119771977https://repository.tcu.edu/handle/116099117/317632,3-Thiophenedicarboxylic anhydride and 2,3-thianaphthene dicarboxylic anhydride were prepared by sequential metal-halogen exchange reactions using n-butyllithium and carbon dioxide on the corresponding dibromides. 3,4-Thiophenedicarboxylic anhydride was prepared by a previously reported method. Although the sealed tube pyrolysis of these anhydrides gave no indication of the corresponding hetarynes, the Flash Vacuum Thermolysis (FVT) of both 2,3-thiophenedicarboxylic anhydride and 2,3-thianaphthenedicarboxylic anhydride in the presence of diene traps gave products which are best rationalized by the intermediacy of a five-membered hetaryne. Products were isolated which correspond to 4+2 Diels-Alder addition reactions. In one case 2,3-thiophyne appears to undergo an ene-reaction with methylacetylene. The 3,4-anhydride failed to react under FVT conditions.vi, 155 leaves, bound : illustrationsFormat: PrintengAnhydridesTextMain Stacks: AS38 .N48 (Regular Loan)Special Collections: AS38 .N48 (Non-Circulating)