Journal of Organic Chemistry p. 8951 - 8953 (2015)
Update date:2022-08-10
Topics:
Tyndall, Stephen
Wong, Koon Fai
Vanalstine-Parris, Melissa A.
The mechanism of the Pechmann condensation is still controversial despite the technological and biochemical importance of coumarins. Here, we present NMR evidence for a mechanism featuring the sequence of initial electrophilic aromatic substitution followed by transesterification and a final dehydration. This mechanism has been convincingly defined and supported by the temporal evolution of two key intermediates which could be purified and identified.
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