Why do some Fischer indolizations fail?
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ABSTRACT:
SUBMITTER: Celebi-Olcum N
PROVIDER: S-EPMC3076556 | biostudies-literature | 2011 Apr
REPOSITORIES: biostudies-literature
Publications
Why do some Fischer indolizations fail?
Çelebi-Ölçüm Nihan N Boal Ben W BW Huters Alexander D AD Garg Neil K NK Houk K N KN
Journal of the American Chemical Society 20110328 15
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. ...[more]
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