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The unusual hydration reactivity of acylketenes: Theoretical and experimental studies

1993; Elsevier BV; Volume: 34; Issue: 7 Linguagem: Inglês

10.1016/s0040-4039(00)77499-5

1873-3581

Annette D. Allen, Michael A. McAllister, Thomas T. Tidwell,

Organic and Inorganic Chemical Reactions

Ab initio MO calculations indicate that the hydration of acylketenes may be assisted by complexation of the nucleophilic H2O molecule to the oxygen of the acyl substituent. Experimental studies for hydration of EtO2CC(Bu-t)=C=O (4) support this pathway.