34421-79-9Relevant academic research and scientific papers
Solvent-promoted E1cB/E2 reactions competing with stepwise solvolysis through homoallylic carbocations
Meng, Qingshui,Thibblin, Alf
, p. 583 - 589 (2007/10/03)
The water-promoted elimination reactions of (R,S)-1-(1-X-ethyl)indene 1-X [X = Cl, Br, I, OBs (4-bromophenylsulfonyloxy)] and the corresponding (R,R) isomers 2-X in 25 vol% acetonitrile in water exhibit non-stereospecific and stereospecific 1,2 elimination, respectively. The reactions are E1cB and E2 type reactions; the conclusion is based upon measured large kinetic deuterium isotope effects and Bronsted β parameters. The rate of the competing solvolytic substitution, which occurs through homoallylic carbocations, increases with the leaving group in the order Br-, I- and BsO-. The spontaneous reactions in methanol are slow; the anti stereochemistry increases with increasing basicity of added base and is favored by negative charge of the base.
