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Simple One-Pot Conversion of Alcohols into Nitriles

Hiroyuki Shimojo, Katsuhiko Moriyama, Hideo Togo*

*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email: togofaculty.chiba-u.jp

H. Shimojo, K. Moriyama, H. Togo, Synthesis, 2013, 45, 2155-2156.

DOI: 10.1055/s-0033-1338489 (free Supporting Information)


Abstract

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.

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Oxidative Conversion of Primary Alcohols, and Primary, Secondary, and Tertiary Amines into the Corresponding Nitriles with 1,3-Diiodo-5,5-dimethylhydantoin in Aqueous NH3

S. Iida, H. Togo, Synlett, 2007, 407-410.


Key Words

nitriles, alcohols, tert-butyl hypochlorite, diiodine, 1,3-diiodo-5,5-dimethylhydantoin, TEMPO


ID: J66-Y2013