41563-67-1Relevant academic research and scientific papers
Metacyclophanes and Related Compounds. Part 16. Preparation of 8-Fluoro-t-butylmetacyclophanes and their Treatment with Aluminium Chloride-Nitromethane in Benzene
Yamato, Takehiko,Arimura, Takashi,Tashiro, Masashi
, p. 1 - 8 (2007/10/02)
The preparation of 8-fluoro-t-butylmetacyclophanes (5) are described.Dithiametacyclophane (3) and metacyclophane bis(sulphones) (4) were obtained as a mixture of transoid and cisoid conformers, but metacyclophanes (5) were exclusively obtained as the transoid conformer after pyrolysis of the sulphones (4).AlCl3-MeNO2-Catalyzed trans-t-butylation of 8-fluoro-16-methyl-5,13-di-t-butylmetacyclophane (5a) in benzene under a variety of conditions faild to give 8-fluoro-16-methylmetacyclophane (32) but, instead, the tetrahydropyrenes (33) and/or (34) were obtained depending upon the conditions used.Internally substituted metacyclophanes were isomerized to the strainless metacyclophanes and these were then oxidized to the tetrahydropyrene (33).
