C-C Bond formation. Chapter 26. Carbon–Carbon Bond Forming Reactions. To form the carbon skeletons of complex molecules, organic chemists need an extensive repertoire of carbon –carbon bond forming reactions.
Alkylation with alkylbromides from organolithium preparation
Elimination reactions with alkylbromides from organolithium preparation or intended alkyl halide
“….the grand thing is to be able to reason backwards. That is a very useful accomplishment, and a very easy one, but people do not practice it much.”
Sherlock Holmes in “A Study in Scarlet”
Break into equal size fragments at branch points or appropriately adjacent to functionality
New monomers for making flame resistant polymers
Advantage over Suzuki Coupling: fewer steps (No boranic ester is needed)
Dye for making fluorescent nanoparticles
Thermal of Lewis acid catalyzed
Noble metal catalyzed
Are precursors available?
Will cross reaction ( R ≠ R’) be dominant
Benzvalene is a less stable isomer of benzene
ΔH = -282 kJ/mole