title: Why do some Fischer indolizations fail?
abstract: 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.
authors: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors: Nihan
authors: N
authors: Çelebi-Ölçüm
authors: Ben W
authors: BW
authors: Boal
authors: Alexander D
authors: AD
authors: Huters
authors: Neil K
authors: NK
authors: Garg
authors: K N
authors: KN
authors: Houk
mesh_terms: D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013816:Thermodynamics
chemical_list: D007211:Indoles; C030374:indole