104488-41-7Relevant academic research and scientific papers
Reaction of Dilithiated Carboxylic Acids with Iodine: Evidence for the Formation of a Radical Anion Intermediate
Renaud, Philippe,Fox, Marye Anne
, p. 3745 - 3752 (2007/10/02)
The mechanism for oxidative dimerization of carboxylic acid dianions involves single electron transfer to iodine, producing an organic anion radical.Rearrangement of this species was observed with suitable substrates at a rate competitive with intermolecular reactions.The radical anion can dimerize or react with iodine.The iodide thus generated can be isolated (reaction with excess of iodine) or can participate in a polar SN2-type reaction sequence leading to dimeric products (reaction with 1/2 equiv of iodine).The interference by free amines (liberated during the metalation with lithium amides) is rationalized by the formation of a charge-transfer complex with iodine which decomposes, liberating protons.
Sterically Hindered Free Radicals, XVI. The Existence of Tetraphenylsuccinic Acid and Its Esters, and the Structure of the Dimers of the Diarylmethyl Radicals Ar2C*-X, X = CO2R, CN, COR
Neumann, Wilhelm P.,Stapel, Ralf
, p. 3422 - 3431 (2007/10/02)
All syntheses of tetraphenylsuccinic acid (esters) described in the literature in fact yield the quinonoids 5 or, after a 1,5-H shift, the benzoids 6. 5 dissociates reversibly giving the radicals Ph2C*-CO2R 4.A real succinic acid derivative, 9, arises, ho
