Reactions
- In the laboratory, solutions of alkyl nitrites in glacial acetic acid are sometimes used as mild nitrating agents. The nitrating species formed is acetyl nitrate generated in situ.
- n-Butyl nitrite and ammonia convert phenylhydroxylamine to its nitrosamine derivative cupferron. Likewise pyrrolidine is a substrate for ethyl nitrite.
- Alkyl nitrites are also used in the formation of oximes with the stronger carbon acids and acid or base catalysis for example in the reaction of 2-butanone, ethyl nitrite and hydrochloric acid forming the oxime, the similar reaction with phenacyl chloride, or the reaction of phenylacetonitrile with methyl nitrite and sodium hydroxide.
An isolated but classic example of the use of alkyl nitrites can be found in Woodward and Doering's quinine total synthesis:
for which they proposed this reaction mechanism:
Read more about this topic: Alkyl Nitrites
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