Base-Catalyzed Decomposition of Acena Phtheneouinone Bissulfonylhydrazones to 1,8-Dicyanonaphthalenes,the Presumed Thermal Chemistry of 1,2,3,4-Tetrazine

In the course of our investigation of the chemistry of diazoacenaphthene, we needed 2-benzylidene-1-diazoacenaphthene (2). As a possible precursor to 2, benzylideneacenaphthenone (1) was treated with one equivalent of tosylhydrazine with the expectation that 2 would be formed following basic decomposition. Surprisingly, acenaphthenequinone bistosylhydrazone (3) was produced instead (Eq. 1).