The reaction of disulfides or thiols with sodium hypochlorite pentahydrate in acetic acid efficiently provided the corresponding sulfonyl chlorides in high yields.

N-Sulfonyloxaziridines (Davis’ oxaziridines) can be synthesized by reacting the corresponding N-sulfonylimines with aqueous sodium hypochlorite in acetonitrile without any catalyst. The pH of the aqueous sodium hypochlorite is crucial to obtain the product in high yield. Optimized conditions are presented that allow synthetically useful Davis’ oxaziridines to be easily obtained in up to 90% yields from the corresponding imines by using inexpensive, stable, environmentally friendly sodium hypochlorite pentahydrate crystals as the oxidant, with high reproducibility.

Oxidation of sulfides with sodium hypochlorite pentahydrate crystals (1.1 equiv) in an aqueous acetonitrile solution selectively produces the corresponding sulfoxides in high yields. This procedure is catalyst-free and environmentally benign.

Crystals. -Oxidation of disulfides or thiols with sodium hypochlorite pentahydrate gives sulfonyl chlorides in an environmentally benign and economical manner. -(OKADA, T.; MATSUMURO, H.; IWAI, T.; KITAGAWA, S.; YAMAZAKI, K.; AKIYAMA, T.; ASAWA, T.; SUGIYAMA, Y.; KIMURA, Y.; KIRIHARA*, M.; Chem. Lett. 44 (2015) 2, 185-187, http://dx.doi.org/10.1246/cl.140899 ; Dep. Mater. Sci., Shizuoka Inst. Sci. Technol., Fukuroi, Shizuoka 437, Japan; Eng.) -B. Mosebach 33-121