Chemistry Letters, Vol.43, No.10, 1548-1550, 2014
Nucleophilic Substitution in 16 pi-Antiaromatic System: Synthesis of Heteroatom-substituted Dibenzopentalenes
An antiaromatic compound, 5-bromo-10-iododibenzopentalene, underwent nucleophilic substitution of heteroatoms such as R2NLi, ROLi, and RSLi. This substitution proceeded preferentially at the bromopentalene moiety than at the iodo-counterpart. Combining this substitution and Sonogashira coupling enabled syntheses of pi-systems expanded by a dibenzopentalene array and heteroatom(s).