N-Pyrrolylketene: A Nonconjugated Heteroarylketene
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
17, evidently by trapping of 2-(1-pyrrolylketene)(21), formed by a new vinylogous Wolff …
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
17, evidently by trapping of 2-(1-pyrrolylketene)(21), formed by a new vinylogous Wolff …
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 17, evidently by trapping of 2-(1-pyrrolylketene) (21), formed by a new vinylogous Wolff rearrangement.
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