Why do some Fischer indolizations fail?

J Am Chem Soc. 2011 Apr 20;133(15):5752-5. doi: 10.1021/ja201035b. Epub 2011 Mar 28.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Models, Molecular
  • Thermodynamics

Substances

  • Indoles
  • indole