Editing Enamine (section)

===Alkylation===
Even though enamines are more nucleophilic than their enol counterparts, they can still react selectively, rendering them useful for alkylation reactions. The enamine nucleophile can attack [[haloalkanes]] to form the alkylated [[iminium]] salt intermediate which then hydrolyzes to regenerate a ketone (a starting material in enamine synthesis). This reaction was pioneered by [[Gilbert Stork]], and is sometimes referred to by the name of its inventor (the [[Stork enamine alkylation]]). Analogously, this reaction can be used as an effective means of [[acylation]]. A variety of alkylating and acylating agents including benzylic, allylic halides can be used in this reaction.<ref>{{cite book|last1=Wade|first1=L.G.|title=Organic Chemistry|url=https://archive.org/details/organicchemistry00wade_1|url-access=registration|date=1999|publisher=Prentice Hall|location=Saddle River, NJ|pages=[https://archive.org/details/organicchemistry00wade_1/page/1019 1019]|isbn=9780139227417}}</ref>
:{{chem2|R2N\sCH\dCHR' +  R"X -> [R2N+\dCH\sCHR'R"]X-}}  (alkylation of enamine)
:{{chem2|[R2N+\dCH\sCHR'R"]+X-  + H2O ->  R2NH  + R'R"CHCHO}}  (hydrolysis of the resulting iminium salt, giving a 2-alkylated aldehyde)