Kinetic applications of electron paramagnetic resonance spectroscopy. 36. Stereoelectronic effects in hydrogen atom abstraction from ethers

V Malatesta, KU Ingold

Index: Malatesta, V.; Ingold, K. U. Journal of the American Chemical Society, 1981 , vol. 103, # 3 p. 609 - 614

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Citation Number: 197

Abstract

Abstract: Relative rates of hydrogen atom abstraction by photogenerated tert-butoxyl from a variety of cyclic and acyclic ethers, acetals, and orthoformates have been measured at-60'C by an EPR spectroscopic technique. There is a pronounced stereoelectronic effect which produces high rates of abstraction from those CH bonds adjacent to oxygen which have a relatively small dihedral angle (ca. 30') with respect to the ptype orbital (s) on the oxygen ( ...