On the metalation of 2,6-dimethyl-4-tert-butyl-thiophenol

摘要

Metalation of 2,6-Dimethyl-4-tert-butyl-thiophenol (6) with n-BuLi/TMEDA in THF occurs regioselectively at the benzylic positions to produce lithium 2,6-di(lithiomethyl)-4-tert-butyl-benzenethiolate (7). Treatment of compound 7 with elemental sulfur followed by iodine-oxidation affords an oxidation product 9a of bis(sulfanylmethyl)-4-tert-butyl-thiophenol (5). [References: 10]