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Allyl Sulfoxides as Precursors for Radical Two-Carbon Ring Expansion of Cyclobutanones
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2002
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Cross-coupling ReactionHeterocyclicAlkene MetathesisBiochemistryRadical Fragmentation–cyclization ProcessUnusual Cascade ReactionNatural SciencesDiversity-oriented SynthesisRadical (Chemistry)Allyl SulfoxidesTwo-carbon Ring ExpansionOrganic ChemistryChemistryHeterocycle Chemistry
The two-carbon ring expansion of cycloalkanones is now possible in a two-step procedure. This procedure is based on an unusual cascade reaction that consists of a [2,3]-sigmatropic rearrangement (Mislow–Braverman–Evans rearrangement) of an allylic sulfoxide followed by a radical fragmentation–cyclization process (see scheme; AIBN = azobisisobutyronitrile).