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Paper | Special issue | Vol 86, No. 1, 2012, pp. 515 - 534
Published online: 2nd August, 2012
DOI: 10.3987/COM-12-S(N)50
SYNTHESIS OF BIS-nAPHTHOPORPHYRINS

Hiroki Uoyama, Hiroko Yamada, Tetsuo Okujima, and Hidemitsu Uno*

*Department of Chemistry and Biology, Graduate School or Science and Engineering, Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan

Abstract

Ethanonaphthoporphyrins with a halogen atom at the ζ position were prepared by the [3+1] porphyrin synthesis of halogen-substituted ethanobenz[f]isoindole with a tripyrrane derivative. The halogeno porphyrins were converted to the corresponding ethynyl and pinacolatoboronyl compounds by Sonogashira and borylation reactions, respectively. Suzuki, Sonogashira, and Glaser coupling reactions of these ethanonaphthoporphyrins gave bis-porphyrins connected with no atom, acetylene, and butadiyne, respectively. Retro Diels-Alder reaction of these bis-porphyrins brought about the conversion of bicyclo[2.2.2]octadiene to benzene moieties to give bis-naphthoporphyrins, quantitatively.

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