Synthesis, structure and properties of ethyl naphth[2,3-f]isoindole-1-carboxylate

Aya Seike; Kaoru Yamagami; Yoshimasa Kakitani; Miki Kuwajima; Hiroki Uoyama; Shin-ichi Nagaoka; Takahiro Nakae; Shigeki Mori; Tetsuo Okujima; Hidemitsu Uno

doi:10.1039/C2RA22870J

Synthesis, structure and properties of ethyl naphth[2,3-f]isoindole-1-carboxylate†

Aya Seike,^a Kaoru Yamagami,^a Yoshimasa Kakitani,^a Miki Kuwajima,^a Hiroki Uoyama,^a Shin-ichi Nagaoka,^a Takahiro Nakae,^a Shigeki Mori,^b Tetsuo Okujima^a and Hidemitsu Uno*^a

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^a Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama, 790-8577, Japan
E-mail: uno@ehime-u.ac.jp
Fax: (+) 81-89-927-9610

^b Integrated Center for Sciences, Ehime University, Matsuyama, 790-8577, Japan

Abstract

Ethyl 12-oxo-4,11-dihydro-4,11-ethanonaphth[2,3-f]isoindole-1-carboxylate (2) was prepared from 7-tert-butoxynorbornadiene and quantitatively converted to ethyl naphth[2,3-f]isoindole-1-carboxylate (3) by the thermal or photochemical cheletropic reaction. Ethyl naphth[2,3-f]isoindole-1-carboxylate (3) existed in a 2H-form both in solution and as a solid, and gradually dimerized to give a dianthradiazafulvalene derivative under aerobic conditions.

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Synthesis, structure and properties of ethyl naphth[2,3-f]isoindole-1-carboxylate†

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Synthesis, structure and properties of ethyl naphth[2,3-f]isoindole-1-carboxylate

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