Allyl iodide explained

Allyl iodide (3-iodopropene) is an organic halide used in synthesis of other organic compounds such as N-alkyl-2-pyrrolidones,^[1] sorbic acid esters, 5,5-disubstituted barbituric acids,^[2] and organometallic catalysts.^[3] Allyl iodide can be synthesized from allyl alcohol and methyl iodide on triphenyl phosphite,^[4] Finkelstein reaction on allyl halides,^[5] or by the action of elemental phosphorus and iodine on glycerol.^{[6] [7]} Allyl iodide dissolved in hexane can be stored for up to three months in a dark freezer at -5C before decomposition into free iodine becomes apparent.^[8]

See also

• Allyl
• Allyl alcohol
• Allyl bromide
• Allyl chloride

Notes and References

1. Encyclopedia: Bertleff. Werner. Carbonylation. Ullmann's Encyclopedia of Industrial Chemistry. 2000. 9,14–15. 10.1002/14356007.a05_217. 978-3527306732. When unsaturated amines are carbonylated in the presence of Co₂(CO)₈, N-alkyl pyrrolidinones are obtained. Carbonylation of allyl halides in the presence of primary amines and a rhodium compound affords the same products....If allyl derivatives are carbonylated in the presence of acetylene by means of Ni(CO)₄ and water or methanol at 20 °C, the acetylene adds onto the allyl halide and 2-cis-5-dienoic acids or esters or sorbic acid esters are obtained..
2. Encyclopedia: Wollweber. Hartmund. Hypnotics. Ullmann's Encyclopedia of Industrial Chemistry. 2000. 521. 10.1002/14356007.a13_533. 978-3527306732. Disubstitution of barbituric acids at the 5-position is only possible with highly reactive halides, such as allyl halides..
3. Encyclopedia: Behr. Arno. Organometallic Compounds and Homogeneous Catalysis. Ullmann's Encyclopedia of Industrial Chemistry. 2000. 10. 10.1002/14356007.a18_215. 978-3527306732. Halogen-containing allyl complexes can often be prepared simply from reactions of allyl halides with metal compounds..
4. Book: Patnaik, Pradyot. A Comprehensive Guide to the Hazardous Properties of Chemical Substances 3rd Ed. 2007. John Wiley & Sons. New Jersey. 9780471714583. 141–142.
5. Book: Adams, Rodger. Organic Reactions, Volume II. 1944. John Wiley & Sons, Inc.. New York. 22.
6. Book: Schorlemmer, C.. A manual of the chemistry of the carbon compounds. 1874. Macmillan and Co.. London. 262.
7. Datta. Rasek Lal. The Preparation of Allyl Iodide. Journal of the American Chemical Society. March 1914. 36. 5. 1005–1007. 10.1021/ja02182a023. 15 December 2013.
8. Book: Armarego, Wilfred . Chai. Christina. Purification of Laboratory Chemicals. 2012. Elsevier. Kidlington. 9780123821614. 114.