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Deprotonation of β,β-disubstituted α,β-unsaturated amides - Mechanism and stereochemical consequences.
- Source :
-
Canadian Journal of Chemistry . Oct2006, Vol. 84 Issue 10, p1397-1410. 14p. - Publication Year :
- 2006
-
Abstract
- A detailed study of the lithium dialkylamide induced deprotonation of β,β-disubstituted α,β-unsaturated amides is presented. The preferential γ-Z-deprotonation and stereochemical outcome of substituents on the γ-Z carbon atom are rationalized in terms of a cyclic eight-membered transition state, which is supported by DFT calculations. Analogous deprotonations on cyclohexylidenecarboxamides reveal a delicate balance of the preference for the eight-membered cyclic transition state with the effects of existing substituents on the ring and the intervention of a twist-boat transition state. [ABSTRACT FROM AUTHOR]
- Subjects :
- *PROTON transfer reactions
*AMIDES
*STEREOCHEMISTRY
*LITHIUM
*CARBON
*ATOMS
Subjects
Details
- Language :
- English
- ISSN :
- 00084042
- Volume :
- 84
- Issue :
- 10
- Database :
- Academic Search Index
- Journal :
- Canadian Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24715580
- Full Text :
- https://doi.org/10.1139/V06-112