Deprotonation of methyl-substituted, five-membered aromatic molecules: a surprising case of mixed conjugation, rehybridization, and induction contributions.
Org Lett
; 16(17): 4680-3, 2014 Sep 05.
Article
en En
| MEDLINE
| ID: mdl-25156066
ABSTRACT
Methyl-substituted, six-membered aromatic molecules are deprotonated to benzylic carbanions, which are stabilized by π conjugation. In contrast, deprotonation of 3(5)-methylpyrazole (NH protected) occurs at an endocylic CH group. Computational analyses showed that the reduction of π conjugation in substituted five-membered rings plays a major role, while the reduced bond angles, in addition to the strengthened induction of Csp(2) versus Csp(3), further favor the deprotonation of endocyclic carbon sites rather than that of the methyl group.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2014
Tipo del documento:
Article
País de afiliación:
Estados Unidos