O-alkyl S-3,3-dimethyl-2-oxobutyl dithiocarbonates as versatile sulfur-transfer agents in radical C(sp3)-H functionalization

Boiling of the title compounds in ethereal solvents or cycloalkanes in the presence of a radical initiator leads to radical C(sp(3))-H functionalization, by which a sulfur atom is introduced into the ethereal solvents at the oxygenated carbon atom or into the cycloalkanes. Both acyclic and cyclic ethers, such as [18]crown-6 and [D-8]THF, undergo the sulfur transfer. The reaction is useful for the synthesis of monothioacetals, thiols, and sulfides from simple starting materials.