1239144-91-2Relevant academic research and scientific papers
Conjugate additions, aza-cope, and dissociative rearrangements and unexpected electrocyclic ring closures in the reactions of 2-(2-Pyrrolidinyl)- substituted heteroaromatic systems with acetylenic sulfones
Weston, Mitchell H.,Parvez, Masood,Back, Thomas G.
supporting information; experimental part, p. 5402 - 5405 (2010/09/05)
(Figure presented) The reactions of 2-heteroaryl-substituted pyrrolidines with acetylenic sulfones proceeded via two pathways. The first involves conjugate addition of the pyrrolidine to the acetylenic sulfone to afford a zwitterion, followed by dissociation of the C-N bond and recombination of the resulting carbocation and vinyl anion to afford the corresponding azepine derivative. The second comprises a cascade of conjugate addition, aza-Cope rearrangement and anionic 6π electrocyclic ring-closure steps. The stability of the carbocation intermediate formed by C-N cleavage determines the dominant pathway.
