<i>para</i>-substituted anilines in reactions with tropyl salts and dibenzosuberenol

Abstract

The features of the interaction of para-substituted anilines with tropyl salts and dibenzosuberenol have been studied. By the interaction of para-substituted anilines with tropyl salts (perchlorate or tetrafluoroborate) in an ethanol or tetrahydrofuran medium, the corresponding azomethines were obtained instead of the expected ortho-tropylated anilines. The tropilidene cycle (1,3,5-cycloheptariene cycle) underwent benzilidene narrowing due to an increase in temperature during a chemical reaction. The structurally related tropilidene - dibenzosuberene cycle can be introduced into the ortho position of para-substituted anilines to form stable ortho products. Dibenzosuberenol in an acidic environment is able to interact with ethanol to form an ether.