N-Pyrrolylketene: A nonconjugated heteroarylketene
MR Islami, AD Allen, S Vukovic, TT Tidwell
Index: Islami, Mohammad Reza; Allen, Annette D.; Vukovic, Sinisa; Tidwell, Thomas T. Organic Letters, 2011 , vol. 13, # 3 p. 494 - 497
Full Text: HTML
Citation Number: 13
Abstract
N-Pyrrolylketene (5) is calculated to be destabilized and nonconjugated, with a preferred geometry with the pyrrolyl ring orthogonal to the ketenyl group. Ketene 5 is generated from N- pyrrolylacetic acid (7) with use of Mukaiyama's reagent, and reacts with imines forming β- lactams 10, with a product ratio correlation of log (cis/trans) with σ+. Photolysis of N- diazoacetylpyrrole (14) in MeOH gives methyl N-pyrrolylacetate (15) from 5 and also ester ...
Related Articles:
Pyrrole synthesis using a tandem Grubbs' carbene–RuCl 3 catalytic system
[Dieltiens, Nicolai; Stevens, Christian V.; Vos, David De; Allaert, Bart; Drozdzak, Renata; Verpoort, Francis Tetrahedron Letters, 2004 , vol. 45, # 49 p. 8995 - 8998]
Reactivity of a tetrahedral intermediate in hydrolysis of N??acetylpyrrole
[Cipiciani, Antonio; Savelli, Gianfranco; Bunton, Clifford A. Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 975 - 976]