83026-87-3Relevant academic research and scientific papers
Reaction entre solvant et especes intermediaires apparues lors de l'electroreduction-acylation de la fluorenone et de la fluorenone-anil dans l'acetonitrile
Degrand, Chantal,Belot, Gerard,Compagnon, Paul-Louis,Gasquez, Francoise
, p. 2581 - 2589 (2007/10/02)
The electrogenerated anions CH2CN- induce the conversion of the various reduction-acylation products of fluorenone 1a and its anil 1b in acetonitrile into 1a and 1b; this phenomenon is controlled by the fortuitous introduction of molecular oxygen.The CH2CN- anions catalyse the transformation of 1a and 1b into fluorenylideneacetonitrile (FlC=CHCN) 17, convertible into the nitriles FlC=CH(CN)=C(NH2)CH3 8, FlC=C(CN)CHFl 10, and FlC(CN)CH2CN 11.These observations allow us to interpret the formation of the products appearing during the electrolysis of fluorenone in acetonitrile in the presence of an equivalent of chloride or anhydride of ω-chloro acid.The products of reduction-acylation appear successively, followed by the nitriles, FlC(OH)CH2CH2CN 3a, 10, FlC(OH)CH2CN 24, and polymers.Because of its basicity the fluorenone radical anion promotes reactions with the solvent, olefin 17 being a preferred intermediate.Bis-fluorenol, fluorenol, and finally fluorene and found with 1a and the above products.
