Intramolecular charge-transfer-induced chemiluminescent decomposition of 1,2-dioxetanes bearing a phenylmethanide anion |
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Authors: | Nobuko Watanabe |
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Institution: | Department of Materials Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293, Japan |
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Abstract: | Dioxetanes (1) bearing a phenyl moiety substituted with a methylene or methine having an electron-withdrawing group(s) (-CH2-Ew or -CH(X)-Ew) and dioxetane (2) bearing a 3-(1-cyanoethenyl)phenyl group were synthesized. Treatment of dioxetanes (1) with tetrabutylammonium fluoride (TBAF) caused their decomposition with accompanying emission of light with maximum wavelength at 530-758 nm. The Michael addition of a bis(methoxycarbonyl)methanide anion to dioxetane (2) produced initially an unstable dioxetane bearing a phenylmethanide anion, decomposition of which gave light with maximum wavelength at 710-740 nm. Intramolecular cyclopropanation without decomposition of the dioxetane ring took place concurrently for the Michael reaction-induced decomposition of 2 with the bis(methoxycarbonyl)chloromethanide anion. |
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Keywords: | Dioxetane Chemiluminescence Carbanion Michael addition Cyclopropanation |
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