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- W2150998907 abstract "Abstract In this paper we describe a new class of antiaromatic planar cyclooctatetraenes: the diazadioxa[8]circulenes. The synthesis was achieved by means of a new acid‐mediated oxidative dimerization of 3,6‐dihydroxycarbazoles to yield the diazadioxa[8]circulenes in high yields. The synthetic protocol appears to be general, and is a one‐pot transformation in which two CC bonds and two CO bonds are formed with the loss of two molecules of water. We also present a detailed characterization of the optical and electrochemical properties of this new class of stable planar cyclooctatetraenes. The properties of the diazadioxa[8]circulenes are compared with the properties of isoelectronic tetraoxa[8]circulenes and azatrioxa[8]circulenes. We discuss the antiaromatic nature of the planar central cyclooctatetraene moiety. The antiaromatic nature of the planar cyclooctatetraenes was studied by using computational methods (NICS calculations), and these calculations reveal that the central eight‐membered ring has antiaromatic character." @default.
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- W2150998907 date "2013-11-05" @default.
- W2150998907 modified "2023-10-18" @default.
- W2150998907 title "Diazadioxa[8]circulenes: Planar Antiaromatic Cyclooctatetraenes" @default.
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- W2150998907 doi "https://doi.org/10.1002/chem.201303194" @default.
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