Repozytorium
Wyszukaj
Kolekcje
Inne
N-Acyl-glutarimides: resonance and proton affinities of rotationally-inverted twisted amides relevant to N–C(O) cross-coupling.
Autorzy
Rok wydania
2018
Czasopismo
Numer woluminu
20
Strony
1342-1345
DOI
10.1021/acs.orglett.8b00086
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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.
Adres publiczny
http://dx.doi.org/10.1021/acs.orglett.8b00086
Strona internetowa wydawcy
Podobne publikacje
Twisted N-acyl-hydantoins: rotationally inverted urea-imides of relevance in N—C(O) cross-coupling.
Szostak Roman, Liu Chengwei, Lalancette Roger, Szostak Michal
Ground-state distortion in N-acyl-tert-butyl-carbamates (Boc) and N-acyl-tosylamides (Ts) : twisted amides of relevance to amide N−C cross-coupling.
Szostak Roman, Shi Shicheng, Meng Guangrong, Lalancette Roger, Szostak Michal
N-Acyl-glutarimides: effect of glutarimide ring on the structures of fully perpendicular twisted amides and N–C bond cross-coupling.
Rahman Md. Mahbubur, Liu Chengwei, Bisz Elwira, Dziuk Błażej, Lalancette Roger, Wang Qi, Chen Hao, Szostak Roman, Szostak Michal