In a complete series of substitution reactions (such as halogenation, nitration, mercuration, etc.,) of furfural and its derivatives, it appears that substitution is preceded by addition. For example, in bromination, two atoms of bromine first add to give a relatively unstable intermediate which then loses hydrogen bromide. These preliminary additions may be 1, 2- or 1, 4- or 1, 6- additions depending upon reactants and upon experimental conditions. Accompanying some of these transformations are ring fission and ring closure, and rearrangements involving unsaturated linkages. Typical illustrations of these changes were presented.
Proceedings of the Iowa Academy of Science
©1930 Iowa Academy of Science, Inc.
Gilman, Henry; Wright, G. F.; Dickey, J. B.; and Hewlett, A. P.
"Mechanisms of Addition and Substitution Reactions of Furfural and Derivatives,"
Proceedings of the Iowa Academy of Science, 37(1), 247-248.
Available at: https://scholarworks.uni.edu/pias/vol37/iss1/48