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• W2046262188 abstract "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." @default.
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• W2046262188 date "1997-10-01" @default.
• W2046262188 modified "2023-10-03" @default.
• W2046262188 title "Medium-Sized Cyclophanes. 43.¹ First Evidence for <i>anti</i>−<i>syn</i>-Ring Inversion under the Nitration of 5,13-Di-<i>tert</i>-butyl-8,16-dimethoxy[2.2]metacyclophane" @default.
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• W2046262188 doi "https://doi.org/10.1021/jo970192p" @default.
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