50710-45-7Relevant academic research and scientific papers
(HALOMETHYLFURAN)CARBOXYLIC ESTERS IN THE MICHAELIS-BECKER REACTION
Pevzner, L. M.,Ignat'ev, V. M.,Ionin, B. I.
, p. 658 - 662 (2007/10/02)
Chloromethyl derivatives of furancarboxylic esters react with sodium diethyl phosphite only in accordance with the classical Michaelis-Becker scheme, but corresponding (bromoethyl)furans are subjected to nucleophilic as well as halogenophilic attack by the phosphite anion.The C-Br bond in 2-(bromomethyl)furans is polarized under the influence of the ring much more strongly than in 3-(bromomethyl) derivatives.The composition of products of the reaction between 2-(bromomethyl)furans and sodium diethyl phosphite shows that halogenophilic attack takes place only if the bromomethyl group is conjugated with the ethoxycarbonyl, the action of the latter being transmitted better from the 5 position than from the 3 position. 3-(Bromomethyl)furans give dehalogenation products only if the ethoxycarboxylic group is in the 2 position.Its influence from the 4 position is transmitted more weakly, and in this case halogenophilic attack does not occur.
