A novel type rearrangement in cyclic β-dicarbonyl compounds in strong acid media
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 reaction mechanism is proposed.
2013 ◽
Vol 295-298
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pp. 326-330
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1970 ◽
Vol 35
(4)
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pp. 1187-1190
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2018 ◽
Vol 83
(5)
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pp. 2904-2911
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1982 ◽
pp. 1107
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2000 ◽
Vol 147
(8)
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pp. 2981
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