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|Section8= }} Allyl cyanide is an organic compound with the formula CH2CHCH2CN. Like other small alkyl nitriles, allyl cyanide is soluble in organic solvents. Allyl cyanide occurs naturally as an antifeedant and is used as a cross-linking agent in some polymers.〔http://encyclopedia2.thefreedictionary.com/allyl+cyanide〕 Allyl cyanide was discovered in 1863 by H. Will and W. Koerner in 1863, they found the compound to be present in mustard oil.〔C. Pomeranz: "Ueber Allylcyanid und Allylsenföl", in: Justus Liebigs Annalen der Chemie, 1906, 351 (1–3), P. 354–362: doi:10.1002/jlac.19073510127〕 The first successful synthesis of allyl cyanide was done by A. Claus in 1864.〔A. Claus: "Ueber Crotonsäure", in: Justus Liebigs Annalen der Chemie, 1864, 131 (1), P. 58–66;doi:10.1002/jlac.18641310106〕 Recent studies show that allyl cyanide may be used as an additive in propylene carbonate-based electrolytes for graphite anodes preventing exfoliation of the anode by film-forming. The underlying mechanism is thought to be a reductive polymerization mechanism.〔L. Zhang et al. Allyl cyanide as a new functional additive in propylene carbonate-based electrolyte for lithium-ion batteries Iconics August 2013, Volume 19, Issue 8, pp 1099-1103〕 ==Synthesis== Allyl cyanide can be prepared by treating allyl bromide with copper(I) cyanide under rigorous heating. This reaction follows a classical SN2 reaction, where the cyanide anion of the copper(I) complex acts as a nucleophile to replace the bromide from the allyl bromide. :CH2=CHCH2Br + CuCN → CH2=CHCH2CN + CuBr Other allyl halides may be used for this reaction including allyl iodide as done by A. Rinne and B. Tollens in 1871 where iodide is a better leaving group than its bromide equivalent and therefore increases the yield.〔A. Rinne, B. Tollens: "Ueber das Allylcyanür oder Crotonitril", in: Justus Liebigs Annalen der Chemie, 1871, 159 (1), S. 105–109; doi:10.1002/jlac.18711590110〕 Another way to gain allyl cyanide is to use rat intestinal microbiota. By adding sinigrin to rat intestinal microbiota and subsequent incubation under anaerobe conditions, this will lead to desulfosinigrin. Further incubation yields allyl cyanide as the major degradation product. More degradation products are isothiocyanate and 1-cyano-2,3-epithiopropane. The exact working principle is not yet understood, but it is suggested that intestinal microbiota may utilize thioglucosidase for this reaction.〔Meng Lua, Kei Hashimotob, Yasushi Udab, Corresponding author contact information Volume 44, Issue 4, May 2011, Pages 1023–1028〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Allyl cyanide」の詳細全文を読む スポンサード リンク
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