4.8 Article

Why Do Some Fischer Indolizations Fail?

期刊

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 15, 页码 5752-5755

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AMER CHEMICAL SOC
DOI: 10.1021/ja201035b

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资金

  1. National Institute of General Medical Sciences
  2. National Institutes of Health [GM-36700]
  3. National Science Foundation [CHE-0955864]
  4. DuPont
  5. Boehringer Ingelheim
  6. Eli Lilly

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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.

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