ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 27, Number 2
JKCSEZ 27(2)
April 20, 1983 

Reaction of thianthrene cation radical perchlorate (1) with cumene (4), p-chlorocumene (2), and p-nitrocumene (3) hydroperoxides in acetonitrile at room temperature afforded, inter alia, thianthrene as a common product and 5-(4'-hydroxyphenyl) thianthrenium perchlorate (5) for 4, 5-(5'-chloro-2'-hydroxyphenyl) thianthrenium perchlorate (7) and 5-acetonylthianthrenium perchlorate (6) for 2 and 6 for 3, respectively. Stoichiometry of these reactions showed that 2 moles of 1 gave rise to 1mole of thianthrene and 1 mole of thianthrenium salt (or salts). Nucleophilic reactivity to 1 was found to be in the order of phenol ≫ p-chlorophenol ∼ acetone ≫ p-nitrophenol. Apart from acid-catalyzed heterolytic decomposition of hydroperoxides, small amount of homolytic decomposition products were found from 3 and 4.