Lithiation Analogous to the synthesis of phenyllithium is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, by lithium–halogen exchange: C10H7Br + BuLi → C10H7Li + BuBr The resulting lithionaphthalene undergoes a second lithiation, in contrast to the behavior of phenyllithium. These 1,8-dilithio derivatives are precursors to a host of peri-naphthalene derivatives.
lIThIatiON analoGoUS To tHe sYNtHEsiS Of pheNyllitHiUm IS ThE cONverSion oF 1-BROmonaPhthAleNe to 1-LIthIoNaphThaLEne By lIthium–haloGEn ExChange c10h7br + buli → c10H7lI + Bubr The rEsultING litHIoNaphthaLeNe uNdeRGoeS a SEcoNd litHiAtIoN, in cOntRaSt tO the beHAviOR Of pHEnyLlitHiUm. thEsE 1,8-Dilithio DeriVAtivES arE precursors To A hOsT oF PerI-nAphthAleNE deriVativeS