A novel type rearrangement in cyclic β-dicarbonyl compounds in strong acid media

K Saito, H Yuki, T Ohyama, R Nakane…

Index: Saito, Kimitoshi; Yuki, Hidetaka; Ohyama, Toshiyuki; Nakane, Ryohei; Nagumo, Katsuyuki; Sato, Tadashi Canadian Journal of Chemistry, 1981 , vol. 59, p. 1717 - 1721

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Citation Number: 5

Abstract

5, 5-Dimethylcyclohexane-1, 3-dione and its derivatives were shown to isomerize to give 5, 6-dihydropyran-4-ones on irradiation in FSO3H or 98% H2SO4. The 2, 2-dimethyl derivative, lacking hydrogen on C2, failed to give any products under the same conditions. A similar type of isomerization was also observed with thiolane-2, 4-dione and its derivatives, while no photoisomerization was observed with their nitrogen or oxygen analogs. A possible ...