Iminium ions can react as electrophilic intermediates
المؤلف:
Jonathan Clayden , Nick Greeves , Stuart Warren
المصدر:
ORGANIC CHEMISTRY
الجزء والصفحة:
ص234
2025-05-14
552
We made the point above that the difference in reactivity between an iminium ion and an oxonium ion is that an iminium ion can lose H+ and form an imine or an enamine, while an oxonium ion reacts as an electrophile. Iminium ions can, however, react as electrophiles provided suitable nucleophiles are present. In fact, they are very good electrophiles, and are significantly more reactive than carbonyl compounds. For example, iminium ions are reduced rapidly by the mild reducing agent sodium cyanoborohydride, Na (CN)BH3, while carbonyl compounds are not. An alternative to Na (CN)BH3 is NaBH (OAc)3 (sodium triacetoxyborohydride)—somewhat safer because strong acid can release deadly HCN from Na (CN)BH3.
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