Alkyl nitrites

s (R-NO2).

The first few members of the series are volatile liquids; methyl nitrite and ethyl nitrite are gaseous at room temperature and pressure. The compounds have a distinctive fruity odor. Another frequently encountered nitrite is amyl nitrite.

ynthesis

Organic nitrites are prepared from alcohols and sodium nitrite in sulfuric acid solution. They decompose slowly on standing, the decomposition products being oxides of nitrogen, water, the alcohol, and polymerization products of the aldehyde. [ "n-butyl nitrite" Organic Syntheses, Coll. Vol. 2, p.108 (1943); Vol. 16, p.7 (1936). [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv2p0108 http://www.orgsynth.org/orgsyn/prep.asp?prep=cv2p0108 Link] ]

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 ["Cupferron" Organic Syntheses, Coll. Vol. 1, p.177 (1941); Vol. 4, p.19 (1925) [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv1p0177 Link] ] . Likewise pyrrolidine is a substrate for ethyl nitrite ["2-Pyrrolidinemethanol, α,α-diphenyl-, (±)-" Organic Syntheses, Coll. Vol. 6, p.542 (1988); Vol. 58, p.113 (1978) [http://www.orgsynth.org/orgsyn/pdfs/CV6P0542.pdf Link] ] .
* 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 ["Dimethylglyoxime" Organic Syntheses, Coll. Vol. 2, p.204 (1943); Vol. 10, p.22 (1930) [http://www.orgsynth.org/orgsyn/pdfs/CV2P0204.pdf Link] ] , the similar reaction with phenacyl chloride ["Glyoxylyl chloride, phenyl-, oxime" Organic Syntheses, Coll. Vol. 3, p.191 (1955); Vol. 24, p.25 (1944) [http://www.orgsynth.org/orgsyn/pdfs/CV3P0191.pdf Link] ] . or the reaction of phenylacetonitrile with methyl nitrite and sodium hydroxide ["Benzeneacetonitrile, α- [(1,1-dimethylethoxy)carbonylcarbonyl] oxy] imino] " Organic Syntheses, Coll. Vol. 6, p.199 (1988); Vol. 59, p.95 (1979) [http://www.orgsynth.org/orgsyn/pdfs/CV6P0199.pdf Link] ] .

An isolated but classic example of the use of alkyl nitrites can be found in Woodward's and Doering's quinine total synthesis ["The Total Synthesis of Quinine" R. B. Woodward and W. E. Doering J. Am. Chem. Soc.; 1945; 67(5) pp 860 - 874; DOI|10.1021/ja01221a051] ::

for which they proposed this reaction mechanism:

:

References


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