Halogen-Metal Exchange in 1,2-Dibromobenzene and the Possible Intermediacy of 1,2-Dilithiobenzene Holger F. Bettinger* and Matthias Filthaus Lehrstuhl fu¨r Organische Chemie 2, Ruhr-UniVersita¨t Bochum, UniVersita¨tsstrasse 150, 44780 Bochum, Germany
[email protected] ReceiVed June 19, 2007
TABLE 1. Yields (in %, from GC/MS Analysis) of the Products Obtained from Trapping the Reaction Mixture of 1,2-Dibromobenzene and t-BuLi in Et2O/THF (1:1) at -120 °C with Various Electrophiles EX (See Experimental Section for Detailed Reaction Conditions) entry
EX
condition
7
9
5
5d
7d
1 2 3 4 5 6 7 8 9 10 11 12
TMSOTf TMSCl ICl I2 ICH2CH2I MeOTf SO2(OMe)2 MeI DCl EtOD TMSOTf EtOH/HCl
A A A A A A A A Aa Aa Bb Bb
89 0 0 0 0
