Abstract
The substitution of 9-(α-bromo-α-arylmethylene fluorenes by MeS− and p-TolS− ions in 80% MeCN–20% H2O is a second-order reaction. With MeS−, for the change of the α-aryl group, Hammett's ρ=1·07 in MeCN. The reaction rate decreases on increasing the water content of the medium. The reactions proceed by the AdN–E route and no competitive SN1 reaction was observed. The expected influence of the changes in the substituent, solvent, nucleophile and nucleofuge on the competition between the AdN–E and SN1 reactions was analyzed. © 1997 John Wiley & Sons, Ltd.
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