Hydroperoxynaphthalenones from the mild autoxidation of certain simple 1-alkyl-2-naphthols

Abstract

1-Isopropyl- and 1-cyclohexyl-2-naphthol react with oxygen in benzene at room temperature and in the absence of catalysts or bases to give 1-alkyl-1-hydroperoxynaphthalen-2(1H)-ones in high yield as the sole products. 1-Ethyl-2-naphthol, however, yields a mixture of the analogous hydroperoxide plus the product of O–C coupling of the phenoxyl radical. 1-Benzyl- and 1-methyl-2-naphthol do not react with oxygen under these conditions.