The Journal of Organic Chemistry

Donor-atom effects on relative E2 rate constants for reactions of anions with cyclohexyl bromide

FG Bordwell, SR Mrozack

Index: Bordwell, Frederick G.; Mrozack, Susan Romberg Journal of Organic Chemistry, 1982 , vol. 47, # 24 p. 4813 - 4815

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Citation Number: 6

Abstract

Summary: 2-Naphthoxide oxanions (2-Np0-) and carbazole nitranions (Cb-) react with cyclohexyl bromide in MezSO solution to give cyclohexene, whereas 9-methylfluorene carbanions (g-MeFl-) give substitution and benzenethiolate thianions give both elimination and substitution. The relative order of E2 rate constants for anions of the same basicity is ArS- > 2-Np0-> Cb-> 9-MeFl-.

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