Reaction of Di-t-butyl Thioketone with Aryllithium. Effect of Temperature and Solvent

Di-t-butyl thioketone reacts with phenyllithium affording both C-phenylated and S-phenylated products. The product distribution largely depends on the reaction temperature and solvent: the lower the temperature and the more solvated the counter cation, the larger the yield of the S-phenylated product. Steric effect is also important: 2,6-dimethylphenyllithium affords only S-arylated product. The result has been interpreted in terms of the charge-transfer-intermediate—radical-combination mechanism.