C(9)-C Bonds of 10-Methyl-9-alkyl-9,10-dihydroacridines Acting Like Metal-Carbon Bonds in the Reactions with Electrophiles

Article abstract of DOI:10.1246/cl.1992.1701

The C(9)-C bonds of 10-methyl-9-alkyl-9,10-dihydroacridines (AcrHR: R = CMe2COOMe, CMe(H)COOEt, Bu^t, CHPh2) are readily cleaved by electrophiles (perchloric acid, oxygen, and iodine) in acetonitrile at 298 K, acting like metal-carbon bonds to yield the corresponding alkane, alkyl hydroperoxide, and alkyl iodide, respectively.