- REARRANGEMENT OF 2-ACYL-2-CHLORO-1,3-CYCLOHEXANEDIONES INTO 2-ACYLRESORCINOLS AND 2-ACYL-4-CHLORO-1,3-CYCLOHEXANEDIONES
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2-Acetylresorcinol was prepared in 80-88percent yield from 2-acetyl-1,3-cyclohexanedione by 2-chlorination (excess of NCS in boiling carbon tetrachloride or one equivalent of molecular chlorine in the cold solvent) followed by aromatization in a heated dry solution of hydrogen chloride in dimethylformamide.The scope of the method was extended to the preparation of 2-propionyl- and 2-isobutyrylresorcinol (resp. 79percent and 66percent yield).Application of the method on 2-acryl-5,5-dimethyl-1,3-cyclohexanediones (acyl=acetyl, propionyl, n-butyryl, i-butyryl) affrded the corresponding 2-acyl-4-chlorodimedone derivatives in 40-77percent yields.
- De Buyck, L.,Seynaeve, D.,De Kimpe, N.,Verhe, R.,Schamp, N.
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p. 363 - 370
(2007/10/02)
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- New cyclohexane- and cyclohexene-1,3-diones from tetraacetylethylene
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The new substituted cyclohexane- and cyclohexene-1,3-diones 3-6 and 9, 10, respectively, have been synthesized from tetraacetylethylene 1, through a ring expansion of the cyclopentenone 2.The structures of these products, as well as some features of their
- Celli, Angela M.,Lampariello, Lucia R.,Chimichi, Stefano,Nesi, Rodolfo,Scotton, Mirella
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p. 1327 - 1332
(2007/10/02)
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