Journal of the Chemical Society. Perkin transactions I p. 2657 - 2664 (1980)
Update date:2022-09-26
Topics:
Barton, Derek H. R.
Bringmann, Gerhard
Lamotte, Genevieve
Motherwell, William B.
Motherwell, Robyn S. Hay
Porter, Alexander E. A.
Primary, secondary, and tertiary aliphatic or alicyclic isocyanides are smoothly reduced under radical conditions using tri-n-butylstannane to the corresponding hydrocarbons.The relative ease of reduction is tertiary > secondary > primary.Aromatic isocyanides are not reduced under these conditions.The reduction of isothiocyanates (or isoselenocyanates) by tri-n-butylstannanae also affords hydrocarbons, but here the isocyanides have been shown to be intermediates.The reduction of a compound with isocyanide and xanthate functions in a 1,2-relationship gives a smooth radical fragmentation to furnish an olefin.An efficient synthesis of 2-deoxy-D-glucose starting with glucosamine is described.
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