Metacyclophanes and related compounds. 19. Reaction of 8-methoxy [2.2] metacyclophanes with iodine in benzene solution. A preparative route to pyrenes

M Tashiro, T Yamato, K Kobayashi…

Index: Tashiro, Masashi; Yamato, Takehiko; Kobayashi, Kazumasa; Arimura, Takashi Journal of Organic Chemistry, 1987 ,  vol. 52,  # 15  p. 3196 - 3199

Full Text: HTML

Citation Number: 33

Abstract

When 8-methoxy [2.2] metacyclophanes are treated with iodine in boiling benzene, the corresponding tetrahydropyrenes (8) are obtained in good yield. The AlCl,-catalyzed trans- tert-butylation of 8 effected loss of the tert-butyl group to give loa-c, which were easily dehydrogenated with DDQ to afford the corresponding pyrene derivatives.