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.
The rearrangement of allylic trichloroacetimidates is a well-known transformation, but the corresponding rearrangement of n class="Chemical">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.
Authors: M Haniti S A Hamid; C Liana Allen; Gareth W Lamb; Aoife C Maxwell; Hannah C Maytum; Andrew J A Watson; Jonathan M J Williams Journal: J Am Chem Soc Date: 2009-02-11 Impact factor: 15.419
Authors: Nivedita S Mahajani; Rowan I L Meador; Tomas J Smith; Sarah E Canarelli; Arijit A Adhikari; Jigisha P Shah; Christopher M Russo; Daniel R Wallach; Kyle T Howard; Alexandra M Millimaci; John D Chisholm Journal: J Org Chem Date: 2019-05-30 Impact factor: 4.354