1,3‐Benzyl Migration in Iminium Ions: Evidence for a Fast Free‐Radical Chain Reaction | Zendy

Blank Nancy | Zendy; Straub Bernd F. | Zendy; Opatz Till | Zendy

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1,3‐Benzyl Migration in Iminium Ions: Evidence for a Fast Free‐Radical Chain Reaction

Author(s) -

Blank Nancy,

Straub Bernd F.,

Opatz Till

Publication year - 2011

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201101183

Subject(s) - chemistry , iminium , ion , chain reaction , thermochemistry , radical , radical ion , photochemistry , computational chemistry , organic chemistry , inorganic chemistry

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.

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