Bulletin of the Chemical Society of Japan p. 1149 - 1155 (1985)
Update date:2022-08-03
Topics:
Kuzuya, Masayuki
Noguchi, Akihiro
Mano, Ei-ichi
Okuda, Takachiyo
The reactions of 2-pyridones with benzyne were investigated in order to gain some insight into the structure-reactivity-chemoselectivity relatinoship involved in the tautomeric systems.All reactions examined have resulted in the formation of Diels-Alder and Michael-type adducts.It has been shown that the Diels-Alder reactivities were well correlated with the HOMO energy levels of the 2-pyridone form and the yields of the Michael-type adduct were closely associated with the tautomeric equilibria.In summary, the chemoselectivities of 2-pyridones in the reaction with benzyne were largely affected by the tautomeric properties.
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