The Tropylation of Polyhydric Phenols and the Dehydrogenation of Their Products

Abstract

The tropylation reaction of polyhydric phenols, such as guaiacol, catechol, resorcinol, hydroquinone, 2, 6-dimethoxyphenol, pyrogallol and phloroglucinol, has been carried out. These polyhydric phenols were quite reactive with ethyl tropyl ether or with tropylium ion, and gave mono-, di-, or sometimes tri-tropyl derivatives. The dehydrogenation of tropylpolyhydric phenol methyl ethers gave stable aryltropilium ions. The methoxyphenyltropones and the methoxyphenyl tropolones were also synthesized in good yields starting from the 4-methoxyphenyltropylium ion.