Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides.
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.
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University , Syracuse, New York 13244, United States.
Arijit A
AA
Adhikari
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University , Syracuse, New York 13244, United States.
Tamie
0000-0003-3753-5204
T
Suzuki
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University , Syracuse, New York 13244, United States.
Reesheda T
RT
Gilbert
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University , Syracuse, New York 13244, United States.
Matthew R
MR
Linaburg
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University , Syracuse, New York 13244, United States.
John D
0000-0001-9518-2393
JD
Chisholm
D000081:Acetamides / Q000737:chemistry*; D062845:Chloroacetates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods
D000081:Acetamides; D062845:Chloroacetates; C009528:trichloroacetamide