Quality Control of 1,3-Dimesityl-1H-imidazol-3-ium tetrafluoroborate. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 1,3-Dimesityl-1H-imidazol-3-ium tetrafluoroborate, is researched, Molecular C21H25BF4N2, CAS is 286014-53-7, about Probing the Diastereoselectivity of Staudinger Reactions Catalyzed by N-Heterocyclic Carbenes.
The reaction of ethylphenylketene with 1,3-dimesitylimidazol-2-ylidene (IMes) or 1,3-dimesitylimidazolin-2-ylidene (SIMes) afforded the corresponding azolium enolates in high yields. The two zwitterions were fully characterized by various anal. techniques. Their thermal stabilities were monitored by thermogravimetric anal. and the mol. structure of SIMes·EtPhC=C=O was determined by means of X-ray crystallog. A mechanism was proposed to account for the trans-diastereoselectivity observed in the [2+2] cycloaddition of ketenes and N-protected imines catalyzed by N-heterocyclic carbenes and an extensive catalytic screening was performed to test its validity. The steric bulk of the NHC catalyst markedly affected the cis/trans ratio of the model β-lactam product. The nature of the solvent used to carry out the Staudinger reaction also significantly influenced its diastereoselectivity. Conversely, the nature of the substituent on the N-sulfonated imine reagent and the reaction temperature were less critical parameters.
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Bromide – Wikipedia,
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