1998
DOI: 10.1002/chin.199805045
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ChemInform Abstract: Photoreaction of Halomethyl Substituted Benzocyclic Ketones with Amines: Radical Cyclization and Ring Expansion Reactions Promoted Through Photoinduced Electron‐Transfer Processes.

Abstract: 1998 photochemistry, radiation chemistry, chemoluminescence photochemistry, radiation chemistry, chemoluminescence O 0160 -045Photoreaction of Halomethyl Substituted Benzocyclic Ketones with Amines: Radical Cyclization and Ring Expansion Reactions Promoted Through Photoinduced Electron-Transfer Processes.-The title reaction of ketones like (I) affords especially the corresponding ring expansion products (II) and (V) via a photoinduced electron-transfer reaction between (I) and Tms-CH 2 -NEt 2 . -(HASEGAWA, E.;… Show more

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“…Iunderwent single electron transfer (SET) with A to cleave the C-I bond to afford Ru II and alkyl radical intermediates B. Meanwhile, intermediates B underwent an intramolecular addition-ring opening cascade to give six-membered iminium radical intermediates C,32,55,56 which would further undergo deprotonation to give allylic radical intermediates D. D could be interrupted by Co II to afford alkyl-Co III intermediates, leading to formal β-hydride elimination 57-59 to give conjugated dienamines E and Co III -H.60 Co III -H…”
mentioning
confidence: 99%
“…Iunderwent single electron transfer (SET) with A to cleave the C-I bond to afford Ru II and alkyl radical intermediates B. Meanwhile, intermediates B underwent an intramolecular addition-ring opening cascade to give six-membered iminium radical intermediates C,32,55,56 which would further undergo deprotonation to give allylic radical intermediates D. D could be interrupted by Co II to afford alkyl-Co III intermediates, leading to formal β-hydride elimination 57-59 to give conjugated dienamines E and Co III -H.60 Co III -H…”
mentioning
confidence: 99%