Manivel Pitchai, Nanjundaswamy K.C, Sankar Ulaganathan, Mohammad Javeed, Antonio Ramirez, Pavan Srinivas, Sourav Roy, Sarah C. Traeger, James Mignone, Elizabeth A. Jurica, Kumar B. Pabbisetty, Muthalagu Vetrichelvan, Anuradha Gupta, Arvind Mathur, Michael D. Mandler
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引用次数: 0
Abstract
The Gabriel amine synthesis is a textbook method for the preparation of primary amines from alkyl halides. In this work, we demonstrate a Gabriel amine synthesis with iodo-bicyclopentanes to make aminomethyl bicyclobutanes. DFT studies support the concerted rearrangement of a bicyclo[1.1.1]pentyl to a bicyclo[1.1.0]butyl carbocation, initiated by a carbon–halide dissociation. A carboxamide substituent stabilizes the carbocation intermediate with anchimeric assistance.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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