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Get confused! Benzene?fused doubly N?confused porphyrins showed macrocyclic18? and weak local benzene 6? aromaticity. Protons in the narrow inner cores exchange at a rate of ?1/2 = ca. 8.5?s (see figure).A bicyclo[2.2.2]octadiene(BCOD)?fused bis(dipyrromethane) derivative was reacted with methylal in the presence of trifluoroacetic acid followed by oxidation with chloranil to give a doubly N?confused phlorin derivative, which did not undergo the retro?Diels?Alder reaction extruding an ethylene molecule on heating. In contrast, a 7?tert?butoxybicyclo[2.2.1]heptadiene(7?BuOBCHD)?fused bis(dipyrromethane) yielded benzene?ring?fused doubly N?confused porphyrins by following similar reaction sequences.

» Author: Hidemitsu Uno, Kota Muramatsu, Shogo Hiraoka, Hiroyuki Tahara, Mako Hirose, Eidai Tamura, Tatsumi Shiraishi, John Mack, Nagao Kobayashi, Shigeki Mori, Tetsuo Okujima, Masayoshi Takase

» Reference: doi:10.1002/chem.202000339

» Publication Date: 04/05/2020

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