3531-25-7Relevant academic research and scientific papers
Electroreductive Cyclopropylcarbonylation of Aromatic Ketones and Their Schiff Bases
Belot, Gerard,Degrand, Chantal,Compagnon, Paul-Louis
, p. 325 - 331 (2007/10/02)
Mono- and dicyclopropylcarbonyl derivatives have been obtained by electroreduction of fluorenone, benzophenone, fluorenone anil, and benzophenone anil in the presence of 1 equiv of 4-bromo(or chloro)butyryl chloride (1a or 1b).The electrolyses are carried out in DMF or MeCN according to two methods.In method A, 1a (or 1b) is added dropwise during the electrolysis.In method B, the total amount of 1a (or 1b) is added at the beginning of the experiment.The electrogenerated bases which are necessary to perform the cyclopropylcarbonylation reactions are either theradical anions of the depolarizers or their acylated anions.The distribution of the compounds and their yields, which are moderate, depend on two main factors which are the method applied and the solvent.It is shown that the properties of acid chlorides 1a and 1b differ in DMF and MeCN.The highest yields of cyclopropyl derivatives are reached in MeCN when method B is applied.However, in this solvent the acylation reaction is less specifically orientated than in DMF, and unexpected propionitrile derivatives are isolated.In the case of the anils, results of chemical reduction by alkali metals and electrochemical reduction are compared.
Cyanomethylation during the Electroreduction of Aromatic Carbonyl Compounds in Acetonitrile
Abbot, Elaine M.,Bellamy, Anthony J.,Kerr, John B.,MacKirdy, Iain S.
, p. 425 - 430 (2007/10/02)
The formation of substituted 3-hydroxy-3-phenylpropiononitriles (II), cinnamonitriles (III), 3-phenylpropiononitriles (IV), and 3-phenylglutaronitriles (V) during the electroreduction of acetophenone, benzaldehyde, and benzophenone in acetonitrile has been studied.The factors which influence the distribution of these products and their importance relative to the 'normal' reduction products, pinacols (VII) and carbinols (VIII), have been identified; current density, temperature, and water concentration are the most important.The distribution of acetonitrile-derived products is compared with that found when the corresponding cinnamonitriles (III) are electroreduced.
