Cyclic (aryl)(amido)carbenes: pushing the π-acidity of amidocarbenes through benzannulation

Cyclic(aryl)(amido)carbenes were synthesized, and studied via a combination of experimental and computational approaches. These carbenes undergo dimerization when isolation is attempted, however, are trapped with sulfur, selenium, and [Ir(cod)Cl]. The π-acidity, measured using 77 Se NMR, revealed th...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-10, Vol.55 (82), p.123-1233
Main Authors: Gildner, M. Brenton, Hudnall, Todd W
Format: Article
Language:English
Subjects:
Aromatic compounds
Carbenes
Crystallography
Dimerization
Donors (electronic)
NMR
Nuclear magnetic resonance
Selenium
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Summary:Cyclic(aryl)(amido)carbenes were synthesized, and studied via a combination of experimental and computational approaches. These carbenes undergo dimerization when isolation is attempted, however, are trapped with sulfur, selenium, and [Ir(cod)Cl]. The π-acidity, measured using 77 Se NMR, revealed that these are the most electrophilic singlet carbenes reported to date whereas the TEP measured demonstrated that these carbenes are poor σ donors. Cyclic(aryl)(amido)carbenes were synthesized, and studied via a combination of experimental and computational approaches.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc05280a