An unexpected [1,5]-h shift in the synthesis of nitroanilines.

Org Lett

Department of Process Research, Merck & Co., Inc., R800-B263, P.O. Box 2000, Rahway, New Jersey 07065-0900, USA.

Published: February 2002

Addition of methyl acetoacetate to 2-nitrovinamidinium hexafluorophosphate salts leads to the formation of anilines or phenols in good to excellent yields depending on the alkylamine substituents. Small substituents, e.g., pyrrolidine, lead to the formation of anilines while large substituents, e.g., N,N-diisopropyl, exclusively give phenols. Labeling studies implicate a [1,5]-H shift proceeding with excellent isotopic fidelity.

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http://dx.doi.org/10.1021/ol017149fDOI Listing

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