α-Bromodiazoacetamides–a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C–H insertion reactions

Å Kaupang, T Bonge-Hansen

Index: Kaupang, Asmund; Bonge-Hansen, Tore Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 1407 - 1413

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Citation Number: 11

Abstract

Abstract In this work, we introduce a new class of halodiazocarbonyl compounds, α- halodiazoacetamides, which through a metal-free, ambient-temperature thermolysis perform intramolecular C–H insertions to produce α-halo-β-lactams. When carried out with α- bromodiazoacetamides bearing cyclic side chains, the thermolysis reaction affords bicyclic α- halo-β-lactams, in some cases in excellent yields, depending on the ring size and ...