Sodium Hypochlorite Pentahydrate Crystals (NaOCl•5H2O): A Convenient and Environmentally Benign Oxidant for Organic Synthesis

The novel oxidant of sodium hypochlorite pentahydrate (NaOCl center dot 5H(2)O) crystals is now available for industrial and laboratory use. It is superior to conventional aqueous sodium hypochlorite solutions (aq. NaOCl). The crystalline material is 44% NaOCl and contains minimal amounts of sodium hydroxide and sodium chloride, and the aqueous solution, which is prepared from NaOCl center dot 5H(2)O and water, has a pH of 11-12. Examples of the selective organic synthesis using NaOCl center dot 5H(2)O involve the oxidations of primary and secondary alcohols, selective oxidations to sulfoxide and sulfone, oxidative cleavage of disulfide to sulfonyl chloride and bromide, oxaziridine synthesis, and oxidative dearomatization of phenols.