Rearrangements of Tertiary Amine Oxides. XIII. The Reactions of p-Nitrobenzenesulfenyl Chloride with Pyridine-and α-Picoline N-Oxides

In the reactions of both pyridine and α-picoline N-oxides with p-nitrobenzenesulfenyl chloride, the N–O bonds of the intermediate salts appear to cleave homolytically, and the p-nitrosulfinyl radical which arises from the homolytic cleavage of the N–O bond is considered to be so stable that only the secondary reaction products from the sulfinyl radical, and no heteroring-substituted products, were obtained.