Halogen/metal vs. hydrogen/metal exchange: General or specific site selectivity as exemplified in the camphene series

Article abstract of DOI:10.1002/cber.19971300112

(Z)-(3,3-Dimethylbicyclo[2.2.1]hept-2-ylidene)methyllithium can be readily generated by treatment of (Z)-3-bromomethylene-2,2-dimethylbicyclo[2.2.1]heptane with ferf-butyl-lithium. At -75°C, the organometallic intermediate is configurationally stable and reacts with a variety of electrophiles under stereochemical retention. VCH Verlagsgesellschaft mbH,.