105639-48-3Relevant academic research and scientific papers
The Effect of Light on Electron-Transfer Substitution at a Saturated Carbon Atom
Wade, Peter A.,Morrison, Harry A.,Kornblum, Nathan
, p. 3102 - 3107 (1987)
Quantum yields have been determined for four electron-transfer substitution reactions at a saturated carbon atom: azide and quinuclidine dispacement of chloride ion from p-nitrocumyl chloride, azide displacement of nitrite ion from α,p-dinitrocumene, and displacement of nitrite ion from ethyl α-nitroisobutyrate by the salt of 2-nitropropane.The values range from 3.5 for the quinuclidine-p-nitrocumyl chloride reaction to 6000 for the azide-p-nitrocumyl chloride reaction.A study of the wavelength dependence of the quantum yields supports the view that photochemical initiation involves a charge-transfer complex between the nucleophile and the compound in which substitution takes place
Electron-Transfer Substitution Reactions: Leaving Groups
Kornblum, Nathan,Ackermann, Peter,Manthey, Joseph W.,Musser, Michael T.,Pinnick, Harold W.,et al.
, p. 1475 - 1481 (2007/10/02)
A number of groups that do not participate in SN2 displacement processes are able to function as leaving groups in electron-transfer chain reactions at room temperature; such groups include azide, sulfone, ethers, nitro, quaternary ammonium ions, esters, and thioethers.Even carbanions are able to function as leaving groups as can be seen from fragmentation of carbon-carbon bonds.
Electron-transfer substitution reactions: The p-nitrocumyl system
Kornblum, Nathan,Cheng, Leung,Davies, Thomas M.,Earl, Gary W.,Holy, Norman L.,Kerber, Robert C.,Kestner, Melvin M.,Manthey, Joseph W.,Musser, Michael T.,Pinnick, Harold W.,Snow, Donald H.,Stuchal, Francis W.,Swiger, Roger T.
, p. 196 - 204 (2007/10/02)
Facile substitution reactions at the tertiary carbon of p-nitrocumyl chloride and α,p-dinitrocumene are described. These reactions occur with a wide range of organic and inorganic nucleophiles and are noteworthy for providing novel and powerful means of synthesis; they occur readily under mild conditions, give excellent yields of pure products, and, in contrast to SN2 displacements, are rather insensitive to steric hindrance. They are, therefore, especially valuable for the preparation of highly branched compounds. The view that these are electron-transfer chain processes derives from inhibition studies and, also, from the fact that these reactions are induced by one-electron-transfer agents.
