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Aluminium–isopropanol Reduction of Tert-nitronitriles: an Unusual Structure of the Reduction Products by Andrei V. Stepanov; Electron A. Mistryukov is a Chemistry article available to read on EtoBox.

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The reduction of -nitronitriles with aluminium-isopropanol results in a cyclic product, strongly O-nucleophilic iminonitronium, which is resistant to further reduction. A convenient procedure for the synthesis of tert-nitronitriles using imidazolium salt catalysis of Michael addition of acrylates to sec-nitroalkane has been reported. 1 As these nitronitriles are of interest as starting compounds for biologically active aminobutyric acids and derivatives, methods for nitro group conversion into an amino substituent deserve attention. This work is devoted to a method for nitro group reduction with aluminium amalgam-protic solvent. Corey et al. 2 developed a method, which was extensively used 3-5 to prepare primary amines from primary or secondary nitro aliphatic derivatives. In respect to a particular case of tert-nitronitriles with nitro function at the quaternary carbon, we encountered an interesting deviation of the reaction pathway connected with the position of nitro and nitrile groups in the molecule. All details of the reduction procedure were optimised for nitronitriles 1a,b. † When 1a or 1b in isopropanol were stirred with a calculated quantity of amalgamated aluminium foil

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Author

Andrei V. Stepanov; Electron A. Mistryukov

Publisher

Royal Society of Chemistry; Elsevier ; Elsevier BV (ISSN 0959-9436)

Published

2008

Language

EN

Field

Chemistry (Physical Sciences)