Metalations in hydrocarbon solvents: Derivatives afforded via the benzyne intermediate

ORGN 540

DW. Slocum, donald.slocum@wku.edu, Megan Jackson, Jennifer Carter, Karen Lalonde, and Julia Raymer. Department of Chemistry, Western Kentucky University, 1906 College Heights Blvd., Bowling Green, KY 42101
TMEDA/hydrocarbon solvent solutions containing an equivalent of chlorobenzene afford a unique reaction when treated with n-BuLi. Yields of about 40% of dimethylaniline are possible under certain conditions.

The benzyne intermediate also reacts with certain o-lithio aryl intermediates to form biphenyls. This sequence possesses the potential to retain the resulting 2'-lithio intermediate to provide a site for further derivatization: