Abstract

A summary of the possible electron-transfer reactions between anthracene and the nitrosonium ion, and a convenient and simple method for the synthesis of 9,10-anthraquinone from anthracene, NaNO 2 and CH 3 OH in CH 2 Cl 2 /CF 3 COOH are presented. The suggestion that the formation of 9,10-anthraquinone in the N 2 O 4 nitration of anthracene originates from trapping of the anthracene radical cation by water is demonstrated to be invalid, e.g., by experiments involving H 2 18 O. Instead, 9,10-anthraquinone is suggested to be formed in the N 2 O 4 -based and in other related systems via follow-up reactions to an initial 1,4-addition across the 9,10 positions of anthracene

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