6533b7ddfe1ef96bd12747df
RESEARCH PRODUCT
1,3-Benzyl Migration in Iminium Ions: Evidence for a Fast Free-Radical Chain Reaction
Till OpatzBernd F. StraubNancy Blanksubject
Crossover experimentChemistryLabellingOrganic ChemistryIminiumPhysical and Theoretical ChemistryPhotochemistryChain reactionIondescription
The “exocyclic” 1,3-benzyl shift observed in iminium salts derived from 1-benzyl-1,2,3,4-tetrahydroisoquinolines is related to the “endocyclic” Knabe rearrangement. A crossover experiment, isotopic labelling, the study of initiators and inhibitors as well as DFT calculations of gas-phase model structures provide evidence for a free-radical pathway under kinetic entropy control that is not affected by “slow” radical traps.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-11-04 | European Journal of Organic Chemistry |