Nitration of
5,13-di-tert-butyl-8,16-dimethoxy[2.2]MCP
(metacyclophane = MCP) (1) with various
nitrating reagents led to ipso-nitration at the
tert-butyl group to give
5-tert-butyl-8,16-dimethoxy-13-nitro[2.2]MCP (2), as well as the corresponding
8,16-epoxy[2.2]MCP (4) arising from
intramolecular condensation reaction via anti−syn-ring
inversion of the nitration intermediate. This novel
intramolecular condensation reaction to afford
8,16-epoxy[2.2]MCP (4) was also observed in
the
presence of Nafion-H under chlorobenzene reflux. The mechanism of
the ipso-nitration as well as
the present novel intramolecular condensation reaction is also
discussed.
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