Mechanisms of elimination reactions. XII. Hydrogen isotope effects and the nature of the transition state in eliminations from alicyclic quaternary ammonium salts

WH Saunders Jr, TA Ashe

Index: Saunders,W.H.; Ashe,T.A. Journal of the American Chemical Society, 1969 , vol. 91, p. 4473 - 4478

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Citation Number: 10

Abstract

Abstract: rruns-Cyclohexyl-2-d-trimethylammonium, trans-cyclopentyl-2-d- trimethylammonium, and 3-pentyl-2, 2-dz-trimethylammonium p-toluenesulfonates were prepared. Intramolecular isotope effects were determined for their base-promoted decomposition by measuring the deuterium contents of the product olefins in the mass spectrometer. With hydroxide ion in water at 191 O, kH/kD ran cyclohexyl, 4.33; ...

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