1. Synthesis and Aromaticity of Benzene-Fused Doubly N-Confused Porphyrins
- Author
-
Hiroyuki Tahara, Tatsumi Shiraishi, Eidai Tamura, John Mack, Kota Muramatsu, Tetsuo Okujima, Shogo Hiraoka, Masayoshi Takase, Shigeki Mori, Nagao Kobayashi, Hidemitsu Uno, and Mako Hirose
- Subjects
Ethylene ,Bicyclic molecule ,010405 organic chemistry ,Organic Chemistry ,Chloranil ,Aromaticity ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,Catalysis ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Trifluoroacetic acid ,Molecule ,Benzene ,Derivative (chemistry) - Abstract
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.
- Published
- 2020