Journal of the American Chemical Society

Leaving-group effects and ion-pair intermediates in base-promoted elimination competing with base-catalyzed 1, 3-proton transfer

A Thibblin, P Ahlberg

Index: Thibblin,A.; Ahlberg,P. Journal of the American Chemical Society, 1977 , vol. 99, # 24 p. 7926 - 7930

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Citation Number: 37

Abstract

Abstract: Reaction of 1-(2-X-2-propyl) indene (hlX)(X= CI, OAc, OMe, or Me) with tertiary amines or sodium methoxide in methanol results in base-promoted 1, 2-elimination and/or base-catalyzed 1, 3-proton transfer. On passing from h-1-Me to hI-CI the total reaction rate was found to increase 615 and 470 times using triethylamine or sodium methoxide, respectively. In spite of this large rate increase, the rearrangement rate was found to ...