An Investigation on the Reactions of Naphthocyclopropene

Article abstract of DOI:10.1016/0040-4020(95)00653-P

In order to investigate the reactivity of naphthocyclopropene (2), the reactions with various dienophiles, dienes and electrophiles was examined.Reaction of 2 with tetracyanoethylene, 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione, 1,3-diphenylisobenzofuran and benzyne afforded the insertion products 3,4,6,10.Cheletropic addition of dichlorocarbene to 2 gave 1,1-dichloronaphthocyclobutene (11).Hydrolysis and reductive elimination of 12 provided naphthocyclobutenone (12) and naphthocyclobutene (13), respectively.Naphthocyclopropene reacted with the different electrophiles like acetic acid, HCl, maleic acid, iodine, bromine, ethanol, and hydrogen afforded the corresponding ring-opening products 14, 15, 16, 17, 18, 19, 20 and 21, respectively.