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- W2788051333 abstract "Resonance energies and proton affinities of N-acyl-glutarimides, compared with related twisted acyclic amides of relevance to N–C(O) cross-coupling, are reported. The data demonstrate that amidic resonance in N-acyl-glutarimides practically disappears (ER < 2.8 kcal/mol), while, intriguingly, these amides favor O-protonation despite significant twist. In some cases, N-acyl-glutarimides undergo intramolecular N- to O-acyl migration, indicative of high capacity as acylating reagents. The understanding provided for the high reactivity of N-acyl-glutarimides should facilitate the development of a broadly general N–C(O) amide activation platform." @default.
- W2788051333 created "2018-03-06" @default.
- W2788051333 creator A5044025336 @default.
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- W2788051333 date "2018-02-16" @default.
- W2788051333 modified "2023-10-16" @default.
- W2788051333 title "<i>N</i>-Acyl-glutarimides: Resonance and Proton Affinities of Rotationally-Inverted Twisted Amides Relevant to N–C(O) Cross-Coupling" @default.
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- W2788051333 doi "https://doi.org/10.1021/acs.orglett.8b00086" @default.
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