An oxidation induced by potassium metal. Studies on the anionic cyclodehydrogenation of 1, 1′-binaphthyl to perylene

M Rickhaus, AP Belanger, HA Wegner…

Index: Rickhaus, Michel; Belanger, Anthony P.; Wegner, Hermann A.; Scott, Lawrence T. Journal of Organic Chemistry, 2010 , vol. 75, # 21 p. 7358 - 7364

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Citation Number: 17

Abstract

Oxidative cyclization of 1, 1′-binaphthyl (1) to perylene (2) can be achieved in essentially quantitative yield by the action of three or more equivalents of potassium metal in hot tetrahydrofuran. An overall reaction mechanism is proposed that accounts for all of the experimental observations reported by previous investigators and those from the present studies. The trans-6a, 6b-dihydroperylene dianion (6 2−) is believed to be the pivotal ...