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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 hypoiodite, which is more reactive, can be prepared from tert-butyl hypochlorite and a metal iodide (M. Ishihara, H. Togo, Synthesis, 2007, 1939. DOI).


Recent Literature


Various alcohols were efficiently converted into the corresponding nitriles at room temperature by treatment with tert-butyl hypochlorite, diiodine, or 1,3-diiodo-5,5-dimethylhydantoin (DIH) in the presence of TEMPO, followed by treatment with diiodine and aqueous ammonia. The nitriles were obtained in good yields and high purities by a simple extraction of the reaction mixture with chloroform and subsequent removal of the solvent.
H. Shimojo, K. Moriyama, H. Togo, Synthesis, 2013, 45, 2155-2156.


An efficient, catalytic Hunsdiecker reaction of aliphatic carboxylic acids affords the corresponding chlorodecarboxylation products in high yields under mild conditions in the presence of t-butyl hypochlorite and Ag(Phen)2OTf as catalyst. The reaction exhibits remarkable functional group compatibility.
Z. Wang, L. Zhu, F. Yin, Z. Su, Z. Li, C. Li, J. Am. Chem. Soc., 2012, 134, 4258-4263.


A silver-catalyzed chlorination of benzylic, tertiary, and secondary C(sp3)-H bonds proceeded with as low as 0.2 mol % catalyst loading at room temperature under air atmosphere with synthetically useful functional group compatibility.
J.  Ozawa, M. Kanai, Org. Lett., 2017, 19, 1430-1433.


A silver-catalyzed ring-opening chlorination of cycloalkanols enables a regioselective, efficient, and pratical approach to carbonyl-containing alkyl chlorides with good yields under mild conditions. The chlorinated products are readily transformed into other useful synthetic intermediates and drugs.
F.-Q. Huang, J. Xie, J.-Guo Sun, Y.-W. Wang, X. Dong, L-W. Qi, B. Zhang, Org. Lett., 2016, 18, 684-687.


A straightforward, convenient, and efficient oxidative dimerization of aromatic amines enables an easy access to symmetrical and unsymmetrical azobenzenes under extremely mild conditions using a unique and cost-effective iodinating reagent.
Y. Takeda, S. Okumura, S. Minakata, Synthesis, 2013, 45, 1029-1033.


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.


The combination of tert-butyl hypochlorite, tetrabutylammonium iodide and tetrabutylammonium chloride as oxidation system enables the transformation of ethyl 2-(N-arylcarbamoyl)-2-iminoacetates into the corresponding quinoxalinones in high yield. Oxygen exhibits a beneficial effect on the reaction.
D. Li, Y. Li, W. Yu, Synthesis, 2017, 49, 4283-4291.