Abstract
Treatment of cycloheptanone or 2-cycloheptylidenecycloheptanone with concentrated sulfuric acid, leads to self-condensation accompanied by intramolecular rearrangement and cyclization to give substituted tetrahydrofurans, viz. 2-methyl-2, 3-cyclohexano-4, 5-cyclohepteno-(Δ5)-2, 3, 4, 5-tetrahydrofuran and 2-methyl-2, 3-cyclohexano-5-hydroxy-4, 5-cycloheptano-2, 3, 4, 5-tetrahydrofuran. Self-condensation of ketones with 6-membered rings under the action of concentrated sulfuric acid, proceeding via carbonium ions, and accompanied by contraction to a 5-membered ring, is also characteristic of cycloheptanone, the 7-membered ring of which isomerizes to a 6-membered one.
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Feller, K.L., Svetozarskii, S.V., Samitov, Y.Y. et al. Reaction of cycloheptanone with concentrated sulfuric acid. Chem Heterocycl Compd 2, 493–495 (1966). https://doi.org/10.1007/BF00477501
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DOI: https://doi.org/10.1007/BF00477501