Photochemical Reactivity of 1-Substituted-1-aza-1,4-dienes
Promoted by Electron-Acceptor Sensitizers. Di-π-methane
Rearrangements and Alternative Reactions via Radical-Cation
Intermediates
Diego Armesto
Maria J. Ortiz
Antonia R. Agarrabeitia
Santiago Aparicio-Lara
Mar Martin-Fontecha
Marta Liras
M. Paz Martinez-Alcazar
10.1021/jo026440l.s001
https://acs.figshare.com/articles/journal_contribution/Photochemical_Reactivity_of_1-Substituted-1-aza-1_4-dienes_Promoted_by_Electron-Acceptor_Sensitizers_Di-_-methane_Rearrangements_and_Alternative_Reactions_via_Radical-Cation_Intermediates/3696720
Irradiation of a series of β,γ-unsaturated imines, oxime acetates, and oxime methyl ethers, using
9,10-dicyanoanthrathene (DCA) or dicyanodurene (DCD) as electron acceptor sensitizers, affords
the corresponding cyclopropanes resulting from 1-aza-di-π-methane rearrangements via radical
cations. In some cases, alternative reactions of these intermediates occur to yield nitriles,
dihydroquinolines, dihydronaphthalene derivatives, and cycloaddition products. Some of these
products result from reactions via alkene radical-cation intermediates while others arise by
pathways involving imine radical-cation intermediates. The yields of products formed in these
processes were significantly higher when DCD was used as electron-acceptor sensitizer instead of
DCA.
2002-11-23 00:00:00
dihydronaphthalene derivatives
products result
DCD
imine
DCA
Alternative Reactions
Photochemical Reactivity
oxime methyl ethers
oxime acetates
intermediate
cycloaddition products
electron acceptor sensitizers
alternative reactions