Journal of Chemical Research

Synthesis of 5-tert-butyl-8, 12, 14-trimethyl-and 5-tert-butyl-8, 12, 14, 16-tetramethyl [2.2] metacyclophane and their treatment with lewis acids in benzene

T Shimizu, K Hida, T Yamato

Index: Shimizu, Tomoe; Hida, Katsuhiko; Yamato, Takehiko Journal of Chemical Research, 2009 , # 7 p. 443 - 447

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Abstract

Treatment of 5-tert-butyl-8, 12, 14, 16-tetramethyl [2.2] MCP with AlCl3-MeNO2 in benzene led to trans-tert-butylation to afford 8, 12, 14, 16-tetramethyl [2.2] MCP in good yield along with tert-butylbenzene. On the other hand, the same treatment of 5-tert-butyl-8, 12, 14- trimethyl [2.2] MCP led to transannular cyclisation reaction and isomerisation reaction to afford the corresponding strainless 2-tert-butyl-3a, 6, 8-trimethyl-3, 3a, 4, 5, 9, 10- ...