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tert-Butyl Hypochlorite

tert-Butyl hypochlorite is a versatile and inexpensive oxidizing agent, that allows the conversion of alcohols to ketones, aldehydes to acid chlorides, sulfides to sulfoxides, and hydroxylamines to nitroso compounds. tert-Butyl hypoiodide, which is more reactive, can be prepared from tert-butyl hypochlorite and a metal iodide (M. Ishihara, H. Togo, Synthesis, 2007, 1939. DOI).


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An efficient preparation of 2-imidazolines was achieved from aldehydes and ethylenediamines in the presence of tert-butyl hypochlorite. By this method, 1,3-bis(imidazolin-2-yl)benzene and 2,6-bis(imidazolin-2-yl)pyridine, which act as chiral ligands, could be prepared directly from the corresponding dialdehydes in high yields.
M. Ishihara, H. Togo, Synthesis, 2007, 1939-1942.