Transformations of ortho-quinones in the γ-radiolysis of their solutions in cyclohexane

Abstract

The transformations of 4-tert-butyl-1,2-benzoquinone (I), 3,5-di-tert-butyl-1,2-benzoquinone (II), and 4-methoxy-5-tert-butyl-1,2-benzoquinone (III) in deaerated cyclohexane solutions under exposure to γ-radiation were studied. It was found by chromatography-mass spectrometry and 1H and 13C NMR spectroscopy that the addition of cyclohexyl radicals at the C=O bond in compounds I–III resulted in monoalkyl ethers, whereas cyclic ketal XXI was also formed in the case of compound II. Moreover, quinone I afforded mixed O-and C-alkylation products, and the adduct of cyclohexyl radicals and quinone II at the C=C bond was the source of dimeric products.