Azoxy group

Nonselective attacks at carbon bonded with nitro group and carbon bonded with azoxy group were observed in reactions of 239 with bases in anhydrous acetonitrile (Scheme 161) (98CEJ1023). Reaction of 4,4 -dinitroazoxyfurazan occurred in a similar way (000HAC48). 

Treatment of macrocycle 278 with an excess of Caro s acid resulted in oxidation of all the sulfur atoms to sulfones and the azo group to an azoxy group (Scheme 181) (99MI4). The oxidation product 279 was formed in 42% yield. Products with smaller oxygen contents were obtained using weaker oxidizing agents. 

The most comprehensive modern works on the subject are the relevant volumes of Patai s series The Chemistry of Functional Groups, namely the two volumes on diazonium and diazo groups (Patai, 1978), the two volumes on hydrazo, azo, and azoxy groups (Patai, 1975) and the two Supplement C volumes on triple-bonded groups (Patai and Rappoport, 1983). Supplement C contains chapters on arene- and alkene-diazonium ions and on dediazoniation reactions. 

GL 18] [R 1] [P 19] For a sputtered palladium catalyst, all intermediates except phenylhydroxylamine were identified [60]. Their relative amoimts allowed one to judge the route by which the hydrogenation proceeds. As a result, it was concluded that species containing nitroso, azo and azoxy groups have a strong interaction with the catalyst and so are preferably involved in the reaction course. In contrast, reduction of the hydrazo species was hindered. These assumptions are in line with literature reports. 

The chemistry of the hydrazo, azo and azoxy groups (2 volumes, 3 parts)... 

Chapter 11 - Reduction of Nitro, Nitroso, Azo and Azoxy Groups, Pages 371-396 Index, Pages 397-401... 

The chemistry of the Hydrazo, Azo and Azoxy Groups (Volume 2, 2 parts)... 

S. Patai, The Chemistry of Functional Groups. The Chemistry of the Hydrazo, Azo and Azoxy-Groups, Part 1 2, J. Wiley Sons, London New York Sydney Toronto 1975. 

P.S. Engel J.L. Wood, unpublished work, 1973 24) R.W. Woolfolk, unpublished work 25) R. Shaw, Thermochemistry of Thiols, Chemistry of the Thiol Group , S. Patai, ed, John Wiley, NY, 1973 26) R. Shaw, Thermochemistry of Azo Compounds, Chemistry of Hydrazo, Azo, and Azoxy Groups , S. Patai, ed, John Wiley, NY, 1974... 

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