Conclusions
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1.
We have developed a method for oxidation by oxygen of carbanions obtained from di-and triarylmethanes in the system KOH-DME-18-crown-6-ether. The reaction products are diarylketones and triarylcarbinols.
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2.
Under the reaction conditions, diarylketones (XC6H4)2CO may be converted to triarylcarbinols (X=H, F, Br). Under the same conditions, (NO2C6H4)2 CO is cleaved with formation of p-nitrophenol and p-nitrobenzoic acid.
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3.
In the case of tris(p-nitrophenyl)carbinolate we have shown the exceptionally strong dependence of the stability of the carbinolate on the counterion: potassium carbinolate is cleaved in the presence of O2 with formation of p-NO2C6H4OH and p-NO2C6H4COOH, lithium carbinolate is stable.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimiya, No. 2, pp. 383–391, February, 1983.
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Artamkina, G.A., Grinfel'd, A.A. & Beletskaya, I.P. Oxidation of triaryl- and diarylmethanes by oxygen in the system KOH-dimethoxyethane-18-crown-6-ether and cleavage of triarylcarbinol and diaryl ketone intermediates. Russ Chem Bull 32, 345–352 (1983). https://doi.org/10.1007/BF00957947
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DOI: https://doi.org/10.1007/BF00957947