Draft:Anomeric amide
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In organic chemistry, anomeric amides refer to amides connected to two heteroatoms at the amide nitrogen atom, typically connected to two oxygen atoms or an oxygen atom and a chlorine atom. Much like acetals and aminals, the nitrogen atom experiences anomeric effect from the heteroatoms. Anomeric amides exhibit different reactivities than regular amides, though this effect is not fully attributed to anomeric effects — rather, anomeric here merely refers to the amide being disubstituted by heteroatoms.[1][2][3]
Introduction
[edit]Structure and Bonding
[edit]Synthesis
[edit]Reactions
[edit]HERON
[edit]Nitrogen Deletion
[edit]Halogenation
[edit]References
[edit]- ^ Glover, Stephen A. (1998). "Anomeric amides — Structure, properties and reactivity". Tetrahedron. 54 (26): 7229–7271. doi:10.1016/S0040-4020(98)00197-5.
- ^ Glover, Stephen A.; Rosser, Adam A. (2014). "HERON reactions of anomeric amides: understanding the driving force". Journal of Physical Organic Chemistry. 28 (3): 215–222. doi:10.1002/poc.3322.
- ^ Glover, Stephen A.; Rosser, Adam A. (2018). "Heteroatom Substitution at Amide Nitrogen—Resonance Reduction and HERON Reactions of Anomeric Amides". Molecules. 23 (11): 2834. doi:10.3390/molecules23112834. PMC 6278557. PMID 30384496.
- ^ Kennedy, Sean H.; Dherange, Balu D.; Berger, Kathleen J.; Levin, Mark D. (2021). "Skeletal editing through direct nitrogen deletion of secondary amines". Nature. 593 (7858): 223–227. Bibcode:2021Natur.593..223K. doi:10.1038/s41586-021-03448-9. PMID 33981048.
- ^ Wang, Yu; Bi, Cheng; Kawamata, Yu; Grant, Lauren N.; Samp, Lacey; Richardson, Paul F.; Zhang, Shasha; Harper, Kaid C.; Palkowitz, Maximilian D.; Vasilopoulos, Aristidis; Collins, Michael R.; Oderinde, Martins S.; Tyrol, Chet C.; Chen, Doris; LaChapelle, Erik A.; Bailey, Jake B.; Qiao, Jennifer X.; Baran, Phil S. (2024). "Discovery of N–X anomeric amides as electrophilic halogenation reagents". Nature Chemistry. 16 (9): 1530–1545. Bibcode:2024NatCh..16.1539W. doi:10.1038/s41557-024-01539-4. PMID 38769366.