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Nitrile anion : ウィキペディア英語版 | Nitrile anion Nitrile anions are nitriles lacking a proton at the position α to the nitrile group. They undergo nucleophilic addition and substitution reactions with various electrophiles.〔Arseniyadis, S.; Kyler, K.S.; Watt, D.S. ''Org. React.'' 1984, ''31'', 1–71.〕 Although nitrile anions are functionally similar to enolates, the extra multiple bond in nitrile anions provides them with a unique ketene-like geometry. Additionally, deprotonated cyanohydrins can act as masked acyl anions, giving products impossible to access with enolates alone. The mechanisms of nitrile addition and substitution are well understood; however, strongly basic conditions are usually required, limiting the reaction's synthetic usefulness. ==Mechanism and stereochemistry==
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