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

• Åsmund Kaupang and
• Tore Bonge-Hansen

Beilstein J. Org. Chem. 2013, 9, 1407–1413, doi:10.3762/bjoc.9.157

• cyclic amide side chains. Keywords: α-halo-β-lactam; diazo; halocarbonylcarbene; halogenation; thermolysis; Introduction Diazocarbonyl compounds are popular precursors for carbonylcarbenes and -carbenoids, the synthetic utility of which is thoroughly established through their successful employment in

• reflux: a reaction that plausibly occurs with a free halocarbonylcarbene or a mercury carbenoid as intermediate [45][55][56]. In the case of the α-bromo-β-lactam 5b, the authors reported an exo-diastereoselectivity of 5.25:1. In order to compare the reactivity of other halides in the α-position, we

• quantified by the ratios of cyclopropanation of increasingly substituted ethylenes [28][30][71]. More recently, a two-dimensional carbenic reactivity surface has been established by Brinker and co-workers. Unfortunately, no halocarbonylcarbene has yet been included in these studies [73]. The donation of