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

Shinpei Iida, Hideo Togo*

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

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

DOI: 10.1055/s-2007-967954

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Abstract

Various primary alcohols, and primary, secondary, and tertiary amines were efficiently converted into the corresponding nitriles in good yields by oxidation with 1,3-diiodo-5,5-dimethylhydantoin (DIH) in aqueous ammonia at 60 °C.

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see article for more reactions

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Simple One-Pot Conversion of Alcohols into Nitriles

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

Direct Oxidative Conversion of Alkyl Halides into Nitriles with Molecular Iodine in Aqueous Ammonia

S. Iida, H. Togo, Synlett, 2008, 1639-1642.

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Key Words

primary alcohols, primary amines, secondary amines, tertiary amines, 1,3-diiodo-5,5-dimethylhydantoin, nitriles, aqueous ammonia

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ID: J60-Y2007-0360