Journal of the American Chemical Society

Stepwise mechanisms in the ene reaction of. alpha.,. beta.-unsaturated esters with N-phenyl-1, 2, 4-triazoline-3, 5-dione and singlet oxygen. Intermolecular primary …

Y Elemes, CS Foote

Index: Elemes, Yiannis; Foote, Christopher S. Journal of the American Chemical Society, 1992 , vol. 114, # 15 p. 6044 - 6050

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Citation Number: 57

Abstract

Abstract: Intermolecular primary and secondary isotope effects on the ene reaction of N- phenyl-1, 2, 4-triazoline-3, 5-dione (PTAD) and singlet oxygen (IO2) with deuterium- substituted (E)-2-methylbuten-2-oic (tiglic) acid methyl esters have been determined. In the case of IO2, the primary isotope effect is 1.30-1.49 and the a and/3 secondary isotope effects are near unity, consistent with a stepwise reaction path via a perepoxide intermediate, ...