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 journalArticle

8 Scopus citations

Abstract

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
Volume82
Issue number7
DOIs
StatePublished - Apr 7 2017

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides'. Together they form a unique fingerprint.

  • Cite this