Cycloacylation of chloro-substituted hydroquinone dimethyl ethers with dichloromaleic anhydride


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Аннотация

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).

Авторлар туралы

V. Novikov

G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences

Хат алмасуға жауапты Автор.
Email: shestak@piboc.dvo.ru
Ресей, 159 prosp. 100 let Vladivostoku, Vladivostok, 690022

N. Balaneva

G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences

Email: shestak@piboc.dvo.ru
Ресей, 159 prosp. 100 let Vladivostoku, Vladivostok, 690022

O. Shestak

G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences

Email: shestak@piboc.dvo.ru
Ресей, 159 prosp. 100 let Vladivostoku, Vladivostok, 690022

V. Anufriev

G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences

Email: shestak@piboc.dvo.ru
Ресей, 159 prosp. 100 let Vladivostoku, Vladivostok, 690022

V. Glazunov

G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences

Email: shestak@piboc.dvo.ru
Ресей, 159 prosp. 100 let Vladivostoku, Vladivostok, 690022

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