||It has been suggested that Poppers be merged into this article. (Discuss) Proposed since January 2013.|
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 (3-methylbutyl nitrite).
Alkyl nitrites were initially, and largely still are used as medications and chemical reagents, a practice which began in the late 19th century. In their use as medicine, are often inhaled for relief of angina and other heart-related symptoms of disease. However when referred to as "poppers", alkyl nitrites represent recreational drugs.
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.
- tert-Butyl nitrite has been shown to be an effective reagent for the selective nitration of phenols  and aryl sulfonamides 
- 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.
for which they proposed this reaction mechanism:
- 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 Link
- Chemoselective Nitration of Phenols with tert-Butyl Nitrite in Solution and on Solid Support Organic Letters, Coll. Vol 11, p.4172-4175 (2009)
- Chemoselective Nitration of Aromatic Sulfonamides with tert-Butyl Nitrite Chemical Communications, DOI: 10.1039/C2CC37481A
- Cupferron Organic Syntheses, Coll. Vol. 1, p.177 (1941); Vol. 4, p.19 (1925) Link
- 2-Pyrrolidinemethanol, α,α-diphenyl-, (±)- Organic Syntheses, Coll. Vol. 6, p.542 (1988); Vol. 58, p.113 (1978) Link
- Dimethylglyoxime Organic Syntheses, Coll. Vol. 2, p.204 (1943); Vol. 10, p.22 (1930) Link
- Glyoxylyl chloride, phenyl-, oxime Organic Syntheses, Coll. Vol. 3, p.191 (1955); Vol. 24, p.25 (1944) Link
- [Benzeneacetonitrile, α-(1,1-dimethylethoxy)carbonylcarbonyl]oxy]imino]-] Organic Syntheses, Coll. Vol. 6, p.199 (1988); Vol. 59, p.95 (1979) Link
- 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