Electronic effects on the substitution reactions of benzhydrols and fluorenyl alcohols. Determination of mechanism and effects of antiaromaticity.

摘要: A range of substituted benzhydrols and fluorenols were prepared subjected to acid catalysed methanolysis. Analysis the rates each these processes showed correlation with Hammett σ+ parameters as is consistent significant build-up positive charge adjacent ring. In combination similarity electronic susceptibility processes, data suggest that both reactions proceed through a unimolecular rate-determining step. This shows effect fusion phenyl systems (and hence potentially introducing an antiaromatic carbocation intermediate) only slow rate reaction rather than change mechanism process.