Photochemical Generation of Six- and Five-Membered Cyclic Vinyl Cations
Year: 2006
Type: article
Abstract: The photochemical solvolyses of 4-tert-butylcyclohex-1-enyl(phenyl)iodonium tetrafluoroborate (1) and cyclopent-1-enyl(phenyl)iodonium tetrafluoroborate (2) in methanol yield vinylic ethers and vinylic cycloalkenyliodobenzenes and cycloalkenylbenzene, which are the trapping products of the geometrically destabilized C6-ring and C5-ring vinyl cation with the solvent and with the leaving group iodobenzene. Iodonium salt 2 also yields an allylic ether and allylic cyclopentenyliodobenzenes and cyclopentenylbenzene, which are the trapping products of the C5-ring allylic cation produced from the C5-ring vinyl cation by a hydride shift in a typical carbocationic rearrangement.
Source: The Journal of Organic Chemistry
DOI: 10.1021/jo0518957
Institutions: Leiden University, University of Hyogo, Tokushima University
Language: English
Subfield: Physical and Theoretical Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W2082227451