- Alkyl nitrites
The first few members of the series are volatile
liquids; methyl nitriteand ethyl nitriteare gaseous at room temperature and pressure. The compounds have a distinctive fruity odor. Another frequently encountered nitrite is amyl nitrite.
Organic nitrites are prepared from
alcohols and sodium nitritein sulfuric acid solution. They decompose slowly on standing, the decomposition products being oxides of nitrogen, water, the alcohol, and polymerizationproducts 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] ]
* In the laboratory, solutions of alkyl nitrites in
glacial acetic acidare sometimes used as mild nitrating agents. The nitrating species formed is acetyl nitrate generated in situ.
* n-Butyl nitrite and
ammoniaconvert phenylhydroxylamineto its nitrosaminederivative 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 pyrrolidineis 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 nitriteand hydrochloric acidforming 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 phenylacetonitrilewith methyl nitriteand 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
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