Imine and enamine formation
A primary amine adds to a suitable aldehyde or ketone and dehydration of the carbinolamine produces an iminium intermediate, which can lose an N proton to give an imine.
Key knowledge
A primary amine adds to a suitable aldehyde or ketone and dehydration of the carbinolamine produces an iminium intermediate, which can lose an N proton to give an imine. A secondary amine instead can lose an α-carbon proton from the iminium intermediate, giving an enamine.
Conditions and scope
- The enamine route requires a suitable α hydrogen; acid activates dehydration but extensive amine protonation inhibits nucleophilic addition.
- The reversible mechanism and optimum pH depend on the specific substrate and medium.
Sources · 1
References
Sources retain their recorded scope. A source link alone does not establish verification of every statement.
Evidence and review
Read shared carbinolamine/iminium stages and N-versus-carbon deprotonation; omitted source illustration's amine mislabelling and universal pH optimum.
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Entry details
Permanent link to this entry ↗- Record identity
- uni-chem-imine-enamine
- Revision
- core.1
- Structured reference record
- University core expansion