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Aldol condensation of acetone/acetone d6 over magnesium oxide and lanthanum oxide

1988; Elsevier BV; Volume: 40; Linguagem: Inglês

10.1016/s0166-9834(00)80436-4

1873-3867

Geng Zhang, Hideshi Hattori, Kozo Tanabe,

Chemical Synthesis and Characterization

Aldol condensation was studied by use of acetone d6. In the reaction of a mixture of acetone d0 and d6, H2H exchange, to form acetone d1 and d5, is faster than the production of diacetone alcohol. In the reaction of a mixture of diacetone alcohol d0 and acetone d6, the amount of acetone d5 exceeded the amount of diacetone alcohol d5–d11. An isotope effect of 1.7 was observed for aldol condensation of acetone d0 and d6. These results suggest a slow formation of the CC bond by reaction of the enolate anion with acetone. The isotopic distribution in diacetone alcohol for the reaction of a mixture of acetone d0 and d6 was in good agreement with the calculated values based on the suggested mechanism.