1416319-95-3Relevant academic research and scientific papers
Characterization of the key intermediates of carbene-catalyzed umpolung by nmr spectroscopy and X-Ray diffraction: Breslow intermediates, homoenolates, and azolium enolates
Berkessel, Albrecht,Yatham, Veera Reddy,Elfert, Silvia,Neudoerfl, Joerg-M.
supporting information, p. 11158 - 11162 (2013/10/22)
Caught in the act: Diamino enols, diamino dienols, azolium enolates, and azolium enols are postulated intermediates of the N-heterocyclic carbene catalyzed umpolung of aldehydes and enals. Several of these elusive reaction intermediates were generated wit
Umpolung by N-heterocyclic carbenes: Generation and reactivity of the elusive 2,2-diamino enols (breslow intermediates)
Berkessel, Albrecht,Elfert, Silvia,Yatham, V. Reddy,Neud?rfl, J?rg-M.,Schl?rer, Nils E.,Teles, J. Henrique
, p. 12370 - 12374 (2013/02/23)
54 years later: Saturated imidazolidin-2-ylidenes react with aldehydes to smoothly produce the elusive 2,2-diamino enols A ( Breslow intermediates , first postulated in 1958) of carbene-catalyzed umpolung reactions. The 2,2-diamino enols A react with additional aldehyde in a cross-benzoin reaction. The methylated Breslow intermediates B are accessible by deprotonation of methoxymethyl azolium salts. Copyright
