Thiyl radicals. III. Some reactions of anthracene, 1,2-benzanthracene, and 3,4-benzopyrene with thiols and oxygen

Abstract

Anthracene, 3-mercaptopropionic acid, and oxygen interact in benzene at room temperature yielding 3-(9-anthry1thio)propionic acid (IV), from which anthracene is regenerated by alkaline hydrolysis in the presence of zinc powder. S-(9-anthryl)-N-acetyl-L-cysteine (VI) was similarly formed from anthracene, oxygen, and N-acetyl-L-cysteine, but experiments using L-cysteine were unsuccessful. Although 1-butanethiol and methyl mercaptoacetate each react readily with anthracene and oxygen, pure products could not be isolated. Thioacetic acid and oxygen react with l,2-benzanthracene yielding 10-acetylthio-l,2-benzanthracene (IX) and 9,10-di(acetylthio)-9,10-dihydro-1,2-benzanthracene (X). 3,4-Benzopyrene, when similarly treated, affords 5-acetyl-thio-3,4-benzopyrene (XI) but phenanthrene, pyrene, perylene, and 1,2:5,6-dibenzanthracene remain unaffected. The theoretical and biochemical implications of these results are discussed.