Journal of the American Chemical Society

Enlarged deuterium isotope effects in oxyanion-catalyzed 1, 3 proton transfer competing with 1, 2 elimination as a probe of a common tightly hydrogen-bonded …

A Thibblin

Index: Thibblin, Alf Journal of the American Chemical Society, 1983 , vol. 105, # 4 p. 853 - 858

Full Text: HTML

Citation Number: 18

Abstract

Abstract: The reaction of 1-(2-acetoxy-2-propyl) indene (1-h) or 1-(2-acetoxy-2-propyl)[1, 3- 2H2] indene (1-d) with p-N02PhO-in methanol buffered with p-N02PhOH results in base- catalyzed 1, 3 proton transfer, yielding 3-(2-acetoxy-2-propyl) indene (2h) and 3-(2-acetoxy- 2-propyI)[l, l-2H2] indene (2-d), respectively, in competition with base-promoted 1, 2 elimination producing 1-isopropylideneindene (3-h) and 1-isopropylidene [3-2H] indene ( ...