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Report | Regular issue | Vol 20, No. 6, 1983, pp.1049-1054
Published online, 1st January, 1970
DOI: 10.3987/R-1983-06-1049
Some Reactions of 3-Bromo-4-bromomethyl-7-methoxycoumarin and 3-Bromo-4-methyl-7-methoxycoumarin with Refluxing N,N-Diethylaniline

Vernon G. S. Box and Clement G. Humes

*Department of Chemistry, Mona Campus, University of the West Indies, Mona, Kingston 7, Jamaica


N,N-diethylaniline effectively debrominated 3-bromo-4-methyl-7-methoxycoumarin and 3-bromo-4-bromomethyl-7-methoxycoumarin, at reflux. This and other reactions of the above-mentioned coumarins in refluxing N,N-diethylaniline provided supporting evidence for the mechanism of the fragmentation of simple 4-aryloxy-2-bromobut-2-enoates which occurred during their attempted Claisen rearrangement in refluxing N,N-diethylaniline.