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

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

全文：HTML全文

被引用次数: 37

摘要

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 ...