Journal of Organic Chemistry p. 4597 - 4602 (1980)
Update date:2022-09-26
Topics:
Smith, Mark A.
Weinstein, Barry
Greene, Frederick D.
Several cyclic azo dioxides have been prepared by oxidation of the corresponding diamines with sodium tungstate-hydrogen peroxide in ethanol-water: 4 (related to o,o'-dinitrosobibenzyl), 8 (related to bis(o-nitrosobenzyl)ether), 14 (related to bis(o-nitrosobenzyl)amine), 13 (the trifluoroacetate salt of 14), 12a and 12b (the N-carbomethoxy and N-carbo-tert-butoxy derivatives of 14).In solution the azo dioxides are in equilibrium (Ke) with the corresponding dinitroso forms: Ke increases with decreasing polarity of solvent and with increasing temperature.For azo dioxide 4 in dioxane at 25 deg C Ke = 0.18, Δ H0 = 7.09 +/- 0.47 kcal mol-1, and Δ S0 = 20.4 cal mol-1 deg-1.The azo dioxides decompose at elevated temperatures (>100 deg C); azo dioxide 14 is converted to 2-(o-nitrosobenzyl)indazole (15) in refluxing methylene chloride.
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