Thiyl Radicals. II. Reactions of meso-Substituted Anthracene Derivatives with Oxygen and Mercaptoacetic Acid

Abstract

9-Methyl- and 9-benzylanthracene each react readily with mercaptoacetic acid and oxygen in benzene yielding (9-methyl-10-anthry1thio)acetic acid and(9-benzyl-10-anthry1thio)acetic acid respectively. There is no evidence for hydrogen atom abstraction from the alkyl substituent by free thiyl radicals. 9,10-Dimethylanthracene, when similarly treated, affords α-(carboxymethylthio)-9,10-dimethylanthracene, but 9,10-diphenylanthracene remains unaffected. These results are consistent with the free-radical-chain mechanism previously suggested.1