Abstract
Reaction of 2-bromomethyl-1-(2′-tetrahydropyranyloxy) benzene 3a with tetrachlorocatechol( TCC) in acetone in presence of anhydrous K 2CO 3 resulted in the formation of diastereomeric products to which cis- & trans- 6-chloro-8-hydroxy-8-(2-oxopropyl)spiro[9 H-benzo[ a]xanthen- 9,2′(1′ H) benzofuran]-7(8 H)-one ( 7a & 8a) structures were assigned, along with tetrachlorocatechol ethers ( 5a & 6a). Similar reaction of 3a with tetrabromocatechol( TBC) gave the expected monobromo compounds 7d & 8d along with the ethers 5d & 6d. When the reaction was repeated with substrates 3b–c with TCC/TBC in ketonic solvents(acetone/methyl ethyl ketone), the corresponding compounds 5b–c to 8b–c, 5e–f to 6e–f, 7e–g & 8e–h were obtained. A suitable explanation has been given for the formation of acetonyl compound 6 in this reaction.
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