Shapeshifting Gabriel Amine Synthesis with Iodo-BCPs.

• Tác giả: Anuradha Gupta, Mohammad Javeed, Elizabeth A Jurica, Nanjundaswamy K C, Michael D Mandler, Arvind Mathur, James Mignone, Kumar B Pabbisetty, Manivel Pitchai, Antonio Ramirez, Sourav Roy, Pavan Srinivas, Sarah C Traeger, Sankar Ulaganathan, Muthalagu Vetrichelvan
• Ngôn ngữ: eng
• Ký hiệu phân loại: 973.84 Administrations of James Abram Garfield and Chester Alan Arthur,
• Thông tin xuất bản: United States : The Journal of organic chemistry , 2025
• Bộ sưu tập: NCBI
• ID: 489336

Tóm tắt

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.