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Synthesis 2001; 2001(4): 0544-0546
DOI: 10.1055/s-2001-12348
short paper
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OsO4-Mediated Conversion of Primary Amines to Nitriles

Shouhai Gao* , David Herzig, Binghe Wang
  • *Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, U.S.A.; Fax + 1(919)5 15 37 57; E-mail: Binghe Wang@ncsu.edu
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Publikationsdatum:
31. Dezember 2001 (online)

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Nitriles are very important intermediates in synthetic organic chemistry. Herein, we report our observation that certain primary amines can be converted to nitriles by trimethylamine N-oxide (TMO) under mild conditions in the presence of a catalytic amount of OsO4. Such a reaction could be used for synthetic purposes as well as for the analysis of functional group compatibility in designing reactions involving OsO4.

osmium tetroxide - trimethylamine N-oxide - primary amines - nitriles