Substituent Effects on Two Orthogonal π-Systems in Pseudopericyclic Ring-opening Reactions of 5-Alkoxy-2-aminooxazoles
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Using the density functional theory calculations, the nature of the effects of electron-donating substituents on pseudopericyclic ring-opening reactions of oxazole derivatives have been explained. The reactions involve interactions in two kinds of orthogonal π-systems at the transition states. A 2-amino group interacts with a horizontal π-system at the transition state, while a 5-alkoxy group interacts with a vertical one. Owing to these substituent effects, the barrier of the ring-opening reactions are reduced cumulatively.
- Chemistry Letters
Chemistry Letters 35(11), 1242-1243, 2006-11-05
The Chemical Society of Japan