Ag+-catalyzed rearrangements. XIII. Mechanistic aspects of the silver (I)-promoted rearrangements of tricyclo [4.1. 0.02, 7] heptane derivatives. Deuterium isotope …

LA Paquette, SE Wilson, RP Henzel

Index: Paquette,L.A. et al. Journal of the American Chemical Society, 1972 , vol. 94, p. 7771 - 7779

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Citation Number: 20

Abstract

Abstract: Kinetic deuterium isotope effects have been determined for the Ag+-catalyzed rearrangements of 1, 7-dideuterio-(lb), 1-deuterio-7-methyl-(3b), and 1- trideuteriomethyltricyclo [4.1. 0.02 J] heptanes (8). Dideuterio analog la exhibited a faster rate of isomerization to 1, 3-cycloheptadiene-2, 3-d2 than its protio counterpart, thereby giving rise to an inverse fractionation factor (kH/kD= 0.847). A similar retirrangement of 3b ...