Various [2.2]metacyclophanes were prepared from the corresponding benzene derivatives by using the feri-butyl group as a positional protective function and their nitrations were carried out under various conditions. It was found that nitration of 8,16-dimethyl[2.2]metacyclophane with fuming HN03 afforded only 5-nitro-8,16-dimethyl [2.2]metacyclophane but not 5,13-dinitro-8,16-dimethyl[2.2]metacyclophane. 5-Iodo-13-nitro-8,16-dimethyl [2.2]metacyclophane was obtained by nitration of 5-iodo-and 5,13-diiodo-8,16-dimethyl[2.2]metacyclophane. It was also found that nitration of the [2.2]metacyclophanes having methoxy groups at internal positions 5 and/or 13 afforded the corresponding tetrahydropyrenes. The reaction mechanisms of the above reactions are also described.
Medium-Sized Cyclophanes.Part 17. Formylation of (n.2)Metacyclophanes.-Formylation of cyclophanes, e.g. (I), proceeds para to the methyl substituents. Cyclophanes of type (V) undergo ipso-formylation. -(YAMATO, T.; MATSUMOTO, J.; KABU, S.; TAKEZAKI, Y.; TASHIRO, M.; J.
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