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Issue 9, 2010
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Reversal of regioselectivity (straight vs. cross ring closure) in the intramolecular [2+2] photocycloaddition of phenanthrene derivatives

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Abstract

Intramolecular [2+2] photocycloaddition of aromatic chain imides possessing bis-phenanthrene moieties afforded straight and cross ring closure products. The ratio of cycloadducts was dependent on reaction time and temperature, which resulted in a reversal of regioselectivity. The reaction was proved to involve a retro cycloaddition. The cross ring closure products were formed predominantly in the early stage of the reaction at lower reaction temperature. In contrast, the straight ring closure products were predominant at higher reaction temperature with prolonged irradiation.

Graphical abstract: Reversal of regioselectivity (straight vs. cross ring closure) in the intramolecular [2+2] photocycloaddition of phenanthrene derivatives

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Publication details

The article was received on 12 Jan 2010, accepted on 02 Mar 2010 and first published on 12 Mar 2010


Article type: Paper
DOI: 10.1039/C000179A
Org. Biomol. Chem., 2010,8, 2174-2179

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    Reversal of regioselectivity (straight vs. cross ring closure) in the intramolecular [2+2] photocycloaddition of phenanthrene derivatives

    S. Kohmoto, S. Hisamatsu, H. Mitsuhashi, M. Takahashi, H. Masu, I. Azumaya, K. Yamaguchi and K. Kishikawa, Org. Biomol. Chem., 2010, 8, 2174
    DOI: 10.1039/C000179A

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