An attempted synthesis of 7-Azabenzo [4,5] cyclohepta [de] naphthalene and coronene

Abstract

In 1952, Pullman et. al.,Pullmann,B., Pullmann, A., Berthier, G. and Pontis, J., J. chim. Phys., (1952), 49, 20. after making a theoretical study of a number of polycyclic aromatic hydrocarbons, predicted that pleiadiene (1), acepleiadylene (2), pleiadene (3), and benzo [4,5] cyclohepta [l,2,3-de] naphthalene (4) should be capable of existence and stable. Boekelheide and Vick Boekelheide, V. and Vick, G.K., J. Am. chem. Soc. (1956), 78, 653. have synthesised pleiadiene (1) and acepleiadylene (2), and they have shown that their physical and chemical properties were in agreement with those predicted by calculations based on molecular orbital theory. Synthesis of pleiadene (3) and its acenaphthylene analogue (5) have been reported by Cava and Schlessinger Cava, M.P. and Schlessinger, R.H., J. Am. chem. Soc. (1963), 85, 835. in 1963, and they showed that these compounds were unstable and underwent a Diels-Alder self-condensation reaction to form the dimer.