title: Halogen-metal exchange in 1,2-dibromobenzene and the possible intermediacy of 1,2-dilithiobenzene.
abstract: The one-step high-yield synthesis of 1,2-bis(trimethylsilyl)benzene from 1,2-dibromobenzene using tert-butyllithium and trimethylsilyltriflate is reported. A mechanistic investigation shows that 1,2-dilithiobenzene is not an intermediate in this reaction; the coexistence of trimethylsilyltriflate and tert-butyllithium at very low temperatures allows a sequence of bromine-lithium exchange and subsequent derivatization reactions to operate.
authors.affiliation: Lehrstuhl für Organische Chemie 2, Ruhr-Universität Bochum, Universitätsstrasse 150, 44780 Bochum, Germany. holger.bettinger@rub.de
authors.forename: Holger F
authors.initials: HF
authors.lastname: Bettinger
authors.forename: Matthias
authors.initials: M
authors.lastname: Filthaus
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D001969:Bromobenzenes / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C526562:1,2-bis(trimethylsilyl)benzene; C526561:1,2-dilithiobenzene; D001555:Benzene Derivatives; D001969:Bromobenzenes; D009942:Organometallic Compounds; D014297:Trimethylsilyl Compounds; C102879:1,2-dibromobenzene; D008094:Lithium