O-Nitrobenzenesulfenyl chloride

Cleavage of the S-tert.butyl group with acids is too cumbersome and is better accomplished in two steps, by treatment with o-nitrobenzenesulfenyl chloride followed by reduction of the thus formed mixed disulfide with mer-captoethanol ... 

A soln. of o-nitrobenzenesulfenyl chloride in chloroform added dropwise at room temp, to a soln. of a slight excess of pyridinium n-dodecanethiolsulfonate in the same solvent, and allowed to stand overnight at room temp. w-dodecane-sulfonyl o-nitrophenyl disulfide. Y 90.5%. F. e. s. Y. Abe, T. Nakabayashi, and J. Tsurugi, Bull. Chem. Soc. Japan 44, 2744 (1971). 

Triethylamine added dropwise with stirring and cooling at 0-5° to an ethereal soln. of 1,4-benzoquinone oxime and o-nitrobenzenesulfenyl chloride, and stirring continued for 5 min. 1,4-benzoquinone oxime o-nitrobenzenesulfenate. 

A soln. of o-nitrobenzenesulfenyl chloride in acetic acid containing water irradiated 50 hrs. with the quartz-filtered light of a 125 w. high-pressure Hg-lamp -> orthanilic acid. Y 80%. V. N. R. Pillai, Chem. Ind. 1976, 456. 

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