IV. Summary
- Page ID
- 24551
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When compared to reactions of halogenated carbohydrates or O-thiocarbonyl compounds, radical reactions of nitriles and isonitriles are few in number. The primary reaction for isonitriles is isocyano group replacement by a hydrogen atom. For nitriles the only reaction of significance is internal addition of a carbon-centered radical to a cyano group to form a cyclic imino radical.
Radical reactions can be involved in nitrile and isonitrile synthesis. Isonitriles are formed from reaction of isothiocyanates with tri-n-butyltin hydride. Nitriles are produced by addition of a carbon-centered radical to t‑butyl isonitrile and subsequent elimination of the t-butyl radical.