Solvolysis of N-n-Alkylacridiniums in Phenol and Carboxylic Acids. Primary Carbonium Ions as Possible Intermediates

Article abstract of DOI:10.1021/jo00139a025

N-n-Octyl (1a) and N-n-dodecylacridinium (1b) ions solvolyze in phenol to give mixtures of the n-alkyl phenyl ethers and all the isomeric secondary straight-chain o- and p-alkylphenols.Solvolyses of 1a in carboxylic acids give a mixture of 1-, 2-, 3-, and 4-octyl carboxylic esters.Structures are deduced by GC/MS.Mechanisms are discussed.