84113-61-1Relevant academic research and scientific papers
Polar Effects in Reactions of Carbon-Centered Radicals with Diazonium Salts: Free-Radical Diazocoupling
Minisci, Francesco,Coppa, Fausta,Fontana, Francesca,Pianese, Giuseppe,Zhao, Lihua
, p. 3929 - 3933 (2007/10/02)
Carbon-centered radicals react with diazonium salts by addition, leading under reductive conditions to azo derivatives (free-radical diazocoupling), or by electron-transfer in chain processes.The reaction is highly sensitive to polar effects and it has been investigated by three different processes: (i) alkyl radicals, generated from alkyl iodides, H2O2, Fe(II) salt, and DMSO, have been utilized to develop a new general synthesis of alkylarylazo compounds; (ii) the reaction of aryl radicals with diazonium salts in the presence of Ti(III) or Fe(II) salts has been investigated, also in relation to the fact that the reaction products (azoarenes and biaryls) are often detected as side products in classical organic reactions of diazonium salts, catalyzed by Cu(I) salts, such as the Sandmeyer, Meerwein, and Pschorr reactions; (iii) adducts from addition of aryl radicals to vinyl acetate or vinyl ether react with diazonium salts either by diazocoupling reaction or by electron-transfer; a general synthesis of arylazo compounds has been developed.
ALKALINE ISOMERIZATION OF PHENYLHYDRAZONES TO ALKYLPHENYLDIIMIDES
Kuznetsov, M.A.,Suvorov, A.A.
, p. 1684 - 1691 (2007/10/02)
When solutions pf phenylhydrazones in tri- or tetraethylene glycol are heated in the presence of the corresponding sodium glycolate, they undergo isomerization to alkylphenyldiimidates.There is a marked decrease in the isomerization rate in the transition from the hydrazones of aldehydes to the hydrazones of ketones.With the phenylhydrazones of ketones the reaction takes place almost unambiguously, but in the case of hydrazones of aldehydes it is complicated to an appreciable extent by side processes such as indolization and aminonitrile cleavage.
