Why Do Some Fischer Indolizations Fail?

Why Do Some Fischer Indolizations Fail?

The mechanisms of the Fischer indole synthesis and competing cleavage pathways were explored with SCS-MP2/6-31G(d) and aqueous solvation calculations. Electron-donating substituents divert the reaction pathway to heterolytic N−N bond cleavage and preclude the acid-promoted [3,3]-sigmatropic rearrang...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2011-04, Vol.133 (15), p.5752-5755
Hauptverfasser: Çelebi-Ölçüm, Nihan, Boal, Ben W, Huters, Alexander D, Garg, Neil K, Houk, K. N
Format: Artikel
Sprache:eng
Schlagworte:
Indoles - chemical synthesis
Indoles - chemistry
Models, Molecular
Thermodynamics
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The mechanisms of the Fischer indole synthesis and competing cleavage pathways were explored with SCS-MP2/6-31G(d) and aqueous solvation calculations. Electron-donating substituents divert the reaction pathway to heterolytic N−N bond cleavage and preclude the acid-promoted [3,3]-sigmatropic rearrangement.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja201035b