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Reactions of nitrile anions : ウィキペディア英語版 | Reactions of nitrile anions
Nitrile anions are the conjugate bases of alkyl nitriles. They undergo nucleophilic addition and substitution reactions with various electrophiles.〔Arseniyadis, S.; Kyler, K. S.; Watt, D. S. ''Org. React.'' 1984, ''31'', 1-71. 〕 ==Introduction== Although nitrile anions are functionally similar to enolates, the extra pi 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 anion addition and substitution are well understood; however, strongly basic conditions are usually required, which can limit the synthetic usefulness of the reaction.
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