organolithium reagent

1. vinyl lithium can't be made directly. tetravinyltin was used to make vinyllithium.
2. RLi is not stable in THF at rt, so Et2O was used as the solvent. control temp at 0C or lower.
3. High sodium Li metal is more active than low sodium Li.
4. Argon should be used instead of N2 when store Li wire in bottle, since Li can react with N2.
5. Excess Li can be used and CuCN can be added directly into the reaction mixture containing Li at -40C. The Cu+ won't be reduced by Li metal.
6. broken glass can be added with Li to improve reactivity. it works as a Li surface scratcher.
7. alky lithium is very basic, stable temp is lower than vinyl lithium.