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8391564 
Journal Article 
On the reaction between anthracene and the nitrosonium ion. A simple method for the preparation of 9,10-anthraquinone and some comments on its formation in aromatic nitration 
Radner, F 
1991 
Yes 
Acta Chemica Scandinavica
ISSN: 0904-213X
EISSN: 1902-3103 
Blackwell Munksgaard 
45 
49-55 
English 
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, NaNO2 and CH3OH in CH2Cl2/CF3COOH are presented. The suggestion that the formation of 9,10-anthraquinone in the N2O4 nitration of anthracene originates from trapping of the anthracene radical cation by water is demonstrated to be invalid, e.g., by experiments involving H2180. Instead, 9,10-anthraquinone is suggested to be formed in the N2O4-based and in other related systems via follow-up reactions to an initial 1,4-addition across the 9,10 positions of anthracene.