Per acid oxidation of cy,@-unsaturated aliphatic azo compounds has resulted in the formation of the corresponding a,@-unsaturated aliphatic azoxy compounds. The position of the oxygen atom in the azoxy group has been found to depend on alkyl substitution. Thus, 2-(methy1azo)propene (IV) and 1-(methy1azo)cyclohexene (VI) gave 2-( methyl-NNO-azoxy)propene (V) and 1-(methyl-NNO-azoxy)cyclohexene (VII), respectively. Oxidation of 2-(methylazo)isobutene (VIII) and 2-(methylazo)-3-methyl-2-butene (X) resulted in 1-(methyl-NON-azoxy )isobutene (IX ) and 1-(methyl-N0N-azoxy)-3-methyl-2-butene in mixture, respectively. Ultraviolet, infrared, and nmr spectral data support the structure assignments given for these compounds.
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