Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 14. A useful radical-deamination reaction
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 2657-2664
- https://doi.org/10.1039/p19800002657
Abstract
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-butylstannane 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.This publication has 2 references indexed in Scilit:
- Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 11. Preparation of olefins from vicinal diolsJournal of the Chemical Society, Perkin Transactions 1, 1979
- Reduction of 6α-alkyl-6β-isocyanopenicillanates by tri-n-butyltin hydride. A stereoselective synthesis of 6β-alkylpenicillanatesJournal of the Chemical Society, Chemical Communications, 1979