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Oxidation of 3‐Furfurylcarbinols with Bromine in Acetone‐Water
Author(s) -
Harn PiinJye,
Lin ChuChung,
Wu HsienJen
Publication year - 2008
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200800035
Subject(s) - chemistry , bromine , acetone , furan , isomerization , alkyl , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis
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.