57643-27-3Relevant academic research and scientific papers
REACTIVITY OF CARBANIONS. XVIII. KINETICS OF THE REACTION OF THE ALKALI-METAL SALTS OF CH ACIDS WITH BENZALDEHYDE
Solov'yanov, A. A.,Karpyuk, A. D.,Beletskaya, I. P.,Reutov, O. A.
, p. 1952 - 1963 (2007/10/02)
The addition of the alkali-metal salts of 9-methoxycarbonylfluorene, fluoradene, 1,3-diphenylindene, diphenylacetonitrile, and 9-phenylfluorene at the carbonyl group of benzaldehyde in dimethoxyethane is reversible.In the presence of hexamethylphophorotriamide the addition product (the carbinolate) dissociates to the initial reagents.The rate constants were determined for addition of the free carbanions and ion pairs at the carbonyl group.In all cases the reactivity of the carbanions is higher in the free state than in the ion pair.The ki constant, determined in the reaction of the cesium or potassium salts of the CH acids, increases in the order 9-methoxycarbonylfluorene + the ionic particles are characterized by higher observed reactivity than in the presence of Cs+ and K+, and this is due to association of the lithium ion pairs of the alcoholates and, possibly, coordination of the alkali-metal cation with the oxygen of the carbonyl group in the benzaldehyde.
