10.1021/jo00805a002
The study investigates the reactions of 2-diazoacenaphthenone (1) with various olefins and acetylenes. The researchers found that 1 did not decompose in boiling benzene or toluene but underwent copper-catalyzed thermolysis in boiling toluene to form biacenedione. In boiling xylene, 1 produced biacenedione and a trace amount of acenaphthenequinone ketazine. When 1 reacted with olefins like ethyl acrylate, acrylonitrile, ethyl a-bromoacrylate, and methyl vinyl ketone in refluxing benzene, it yielded spiro[acenaphthenone-2,1'-cyclopropanes] (3a-d, 4a-c, 7) with two stereoisomers for some reactions. Reactions with acrolein, phenylacetylene, and diethyl acetylenedicarboxylate led to the formation of 2'-hydroxymethylspiro[acenaphthenone-2,1'-cyclopropanes] (5, 6) and spiro[acenaphthenone-2,3'(3'H)-pyrazoles] (9, 10). The study also explored the reaction of 1 with bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, producing spiro[acenaphthenone-2,3'-tricyclooctanedicarboxylic anhydride] (8). The researchers used various analytical techniques to confirm the structures and properties of the synthesized compounds.
