Angewandte Chemie International Edition · 1999 · 41 citations · 0 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryHalogen ChemistryHeterocycle SynthesisOrganic SynthesisRadical ReactionsAllylic FunctionalizationBromine Radical ChemistryC - H Bond FunctionalizationChain Carrier SpeciesFree Radical Chain ReactionsHydrogen Atom TransferKinetic Chain AnalysisOrganic Substrates
The Br. radical is the chain carrier of a new highly selective allylation of hydrocarbons (and other substrates): It abstracts a hydrogen atom from R−H to yield R.. Addition of R. to substituted allyl bromide (to form a β-bromo radical) followed by β-cleavage regenerates Br. and provides the product. Reaction yields and kinetic chain lengths for this reaction are highest when the allyl bromide contains a radical-stabilizing substituent.