Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides

Arijit A. Adhikari, Tamie Suzuki, Reesheda T. Gilbert, Matthew R. Linaburg, John D. Chisholm

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


The rearrangement of allylic trichloroacetimidates is a well-known transformation, but the corresponding rearrangement of benzylic trichloroacetimidates has not been explored as a method for the synthesis of benzylic amines. Conditions that provide the trichloroacetamide product from a benzylic trichloroacetimidate in high yield have been developed. Methods were also investigated to transform the trichloroacetamide product directly into the corresponding amine, carbamate, and urea. A cationic mechanism for the rearrangement is implicated by the available data.

Original languageEnglish (US)
Pages (from-to)3982-3989
Number of pages8
JournalJournal of Organic Chemistry
Issue number7
StatePublished - Apr 7 2017

ASJC Scopus subject areas

  • Organic Chemistry


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