216451-99-9Relevant academic research and scientific papers
Rhodium(II)- and copper(I)-catalyzed intramolecular carbon-hydrogen bond insertions with metal carbenoids derived from diazo ketones
Mueller, Paul,Maitrejean, Esther
, p. 1807 - 1826 (2007/10/03)
The decomposition of diazo ketones in the presence of Rh(II) and Cu(I) catalysts affords products of C-H bond insertion in high yields. The effect of structural variation on intramolecular and transannular C-H insertions of diazo ketones has been investig
(Trialkylsilyl)vinylketenes: Synthesis and application as diene components in Diels-Alder cycloadditions
Loebach, Jennifer L.,Bennett, Dawn M.,Danheiser, Rick L.
, p. 8380 - 8389 (2007/10/03)
New strategies for the synthesis of (trialkylsilyl)vinylketenes ('TAS- vinylketenes') are described based on the photochemical Wolff rearrangement of α'-silyl-α'-diazo-α,β-unsaturated ketones and the 4π electrocyclic ring opening of cyclobutenones. These remarkably robust vinylketenes undergo highly regioselective [4 + 2] cycloadditions with reactive olefinic and acetylenic dienophiles to produce highly substituted cyclohexenones and phenols in which the ketene carbonyl dominates in controlling the regiochemical course of the reaction. The stereochemical course of these cycloadditions follows the Alder endo rule, as illustrated in the reaction of nitropropene with TAS-vinylketene 22.
