Specific Features of Reactions of Halomethyl Derivatives of 2-Isobutylfuran with Nucleophiles

3,4- and 3,5-bis(chloromethyl)-2-isobutylfurans react with sodium diethyl phosphite by the Michaelis-Becker reaction scheme to form phosphonates whose yield significantly depends on the location of the halomethyl group in the furan ring. 3,4-Bis(chloromethyl)-2-isobutyl-5-methylfuran under analogous conditions gives a diphosphonate, while in 3,5-bis(chloromethyl)-2-isobutylfuran phosphorylation of the α-chloromethyl group competes with dehydrochlorination leading to a chloromethylated alkene, the second process being preferred. Further phosphorylation involves only one chloromethyl group of the alkene. Ethyl 5-(bromomethyl)-2-isobutylfuran-3-carboxylate reacts with sodium acetate to give a substitution product, while its isomer with the reverse location of the substituents eliminates hydrogen bromide exclusively. In the latter case, the acetate is formed only as a minor product.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 6, 2005, pp. 991–998.Original Russian Text Copyright © 2005 by Pevzner.