Cycloacylation of chloro-substituted hydroquinone dimethyl ethers with dichloromaleic anhydride |
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| Authors: | V. L. Novikov N. N. Balaneva O. P. Shestak V. Ph. Anufriev V. P. Glazunov |
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| Affiliation: | 1.G. B. Elyakov Pacific Institute of Bioorganic Chemistry,Far-Eastern Branch of the Russian Academy of Sciences,Vladivostok,Russian Federation |
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| Abstract: | Under the drastic conditions of Zahn—Ochwat cycloacylation of 2-chloroand 2,3-dichlorohydroquinones with dichloromaleic anhydride (a melt of anhydrous AlCl3 and NaCl, 185—195 °C), the substrates undergo various degrees of disproportionation, which reduces the yields of the target triand tetrachloronaphthazarins. Quantum chemical calculations showed that the cycloacylation in question proceeds as a double aromatic electrophilic substitution of the vicinal protons with the corresponding oxocarbenium ions (acylium cations). |
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