Wolfenstein-Boters reaction

The Wolffenstein-Boters reaction is an organic reaction converting benzene to picric acid by a mixture of aqueous nitric acid and mercury(II) nitrate.^[1]

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According to one series of studies the mercury nitrate first takes benzene to the corresponding nitroso compound and through the diazonium salt to the phenol. From then on the reaction proceeds as a regular aromatic nitration.^[2]^[3]

A conceptually related reaction at one time of interest to the pigment industry is the Bohn-Schmidt reaction (1889) involving the hydroxylation of hydroxyantraquinone with sulfuric acid and lead or selenium to a polyhydroxylated anthraquinone.

References

^ Wolffenstein and Boeters, Chcm. Abs., I, 489, 1861 (1908); 4, 369 (1910); Bcr., 46, 586 (1913)
^ The Mechanism of the Oxynitration of Benzene F. H. Westheimer, Edward Segel, and Richard Schramm J. Am. Chem. Soc.; 1947; 69(4) pp 773 - 785; doi:10.1021/ja01196a011
^ The Oxynitration of Benzene. I. Studies Relating to the Reaction MechanismsMarvin Carmack, Manuel M. Baizer, G. Richard Handrick, L. W. Kissinger, and Edward H. Specht J. Am. Chem. Soc.; 1947; 69(4) pp 785 - 790; doi:10.1021/ja01196a012