133512-49-9Relevant academic research and scientific papers
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, Finn
, p. 49 - 55 (2007/10/02)
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 H218O.Instead, 9,10-anthraquinone is suggested to be formed in the N2O4-based and in other related systems via foll ow-up reactions to an initial 1,4-addition across the 9,10 positions of anthracene.
Benzoquinones and Related Compounds. Part 4. Thermolysis of the Diels-Alder Adduct of 2-Acetyl-5,6-dichloro-1,4-benzoquinone and Cyclopentadiene: Evidence for a Partial Retro-diene Reaction
Beddoes, Roy L.,Bruce, J. Malcolm,Finch, Harry,Heelam, Leslie M. J.,Hunt, Ian D.,Mills, Owen S.
, p. 2670 - 2676 (2007/10/02)
Addition of chlorine to (2-methyl-1,3-dioxolan-2-yl)-1,4-benzoquinone occurs at the unsubstituted double bond.Subsequent enolisation and cleavage of the acetal affords 2-acetyl-5,6-dichlorohydroquinone in 50percent overall yield.Oxidation of this gives the corresponding 1,4-benzoquinone which with cyclopentadiene yields, predominantly, the 1 : 1 Diels-Alder adduct (6) by endo-addition to the 2,3-double bond.Thermolysis of this adduct in benzene results in disproportionation to cyclopentadiene and the spiro-acetal (13); thermolysis in acetic acid also yields (13), but the major product is the dihydrobenzofuran (14), an isomer of the Diels-Alder adduct.Mechanisms for the formation of these products are discussed.
