Oxidation of 3‐Furfurylcarbinols with Bromine in Acetone‐Water

Abstract Oxidation of 3‐furfurylcarbinols 3a‐e and 7 with bromine in acetone‐water solution gave the 2‐substituted‐3‐furfurals 4a‐e and 8 in good yields, respectively. Reaction of 2‐alkyl‐3‐furfurylcarbinols 9a and 9b with bromine in acetone‐water gave the bromoalkyl 3‐furfuryl ketones 10a and 10b as the major products. A reaction mechanism via the cis‐trans isomerization of the 2‐ene‐1,4‐diones 13 and 14 was proposed to account for the transposition of the alkyl group of the 3‐furfurylcarbinols 3, 7 and 9 to the 2‐position on the furan ring of the products 4, 8 and 10.