4352-95-8Relevant articles and documents
A remarkable iodine-catalyzed protection of carbonyl compounds
Banik, Bimal K.,Chapa, Marin,Marquez, Jocabed,Cardona, Magda
, p. 2341 - 2343 (2007/10/03)
We report here a remarkably simple molecular iodine-catalyzed protection method for various carbonyl compounds as ketals in a general reaction. The iodine-catalyzed reaction of mandelic acid and lactic acid with several aldehydes has furnished a highly diastereoselective synthesis of cis and trans dioxolanones.
Radicals through Photoinduced Electron Transfer. Addition to Olefin and Addition to Olefin-Aromatic Substitution Reactions
Mella, Mariella,Fagnoni, Maurizio,Albini, Angelo
, p. 5614 - 5622 (2007/10/02)
The radical cations of 2,2-dialkyl- and 2-alkyl-2-aryl-1,3-dioxolanes, when generated in solution by photoinduced electron transfer to 1,2,4,5-benzenetetracarbonitrile (TCB), fragment to yield alkyl radicals.These are trapped by electron-withdrawing substituted alkenes (acrylonitrile, methyl acrylate, methyl vinyl ketone, as well as dimethyl maleate and fumarate).The radicals thus formed are either reduced by the TCB radical anion or add to it.In the first process (observed only with the diesters) the end result is reductive alkylation of the olefin, while the latter process results in an addition to the olefin-aromatic substitution reaction.The selectivity of the process is explained on the basis of steric hindrance, since the radicals react when still in the cage with the aromatic radical anion.