Solvolysis of 2-substituted-9-(ortho-substituted) phenylmethyl)fluoren-9-yltrimethylammonium ions in various solvents

Article abstract of DOI:10.1139/v86-178

The solvolytic reaction of several 9-(ortho-substituted phenylmethyl)fluoren-9-yltrimethylammonium salts has been investigated in several different solvents.Substitution and elimination products were found for the reactions in all solvents studied, with the exceptions that rection in both tert-butyl alcohol and chloroform led exclusively to the alkene product.The observed rate constants for alkene formation and the percent alkene were measured and it was found that the di-ortho compounds reacted at a faster rate but produced less alkene than the reaction of the corresponding mono-ortho salts.Hydrogen-deuterium isotope effects were also determined for the various reactions.The results are discussed in terms of the reaction proceeding by way of the E1 mechanism, where steric acceleration promotes the loss of the bulky ammonium leaving group to give the carbocation intermediate.