TY - JOUR
T1 - Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides
AU - Adhikari, Arijit A.
AU - Suzuki, Tamie
AU - Gilbert, Reesheda T.
AU - Linaburg, Matthew R.
AU - Chisholm, John D.
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/4/7
Y1 - 2017/4/7
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.7b00245
DO - 10.1021/acs.joc.7b00245
M3 - Article
C2 - 28323428
AN - SCOPUS:85017122323
SN - 0022-3263
VL - 82
SP - 3982
EP - 3989
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -