Abstract
Density functional theory (DFT) was employed to investigate possible mechanisms of aza-Baeyer-Villiger rearrangement reaction of cyclobutanone with aminodiphenylphosphonate. The calculation results show that the reaction involves two processes, including nucleophilic addition on carbonyl carbon coupled with a proton transfer for formation of Criegee-type intermediate and five-membered ring-closure coupled with the other proton transfer. For both the two processes, almost all the possible pathways including water-participated, Ph2PO(ONH2)-participated, Ph2PO(OH)-participated, and direct pathways have been considered and compared to identify main pathway. The Ph2PO(OH)-participated proton transfer pathway is the most energetically favourable in the entire reaction. The gained insights should be helpful for understanding the detailed mechanism for these kinds of reactions.
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