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. 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.

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  • 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. 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. (en)
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  • 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. 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. (en)
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  • Nitrile anion (en)
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