The Olympicenyl Radical and Its Derivatives

The olympicenyl radical (OR) has long been a fascinating spin doublet hydrocarbon radical that evoked theoretical and experimental research interests, but the chemistry of olympicenyl was limited by its inherent instability. Recently, this field was revived by the advent of stable, multi-substituted ORs and the isolation of them in the crystalline phase. In this minireview, we summarize the early studies on the pristine OR, as well as the recent advances on the substituted OR derivatives, heteroatom-containing OR derivatives, and OR-based diradicals and polyradicals. The synthetic chemistry, stabilization strategies, self-association behaviors, reactivities, and applications in the biological field of the abovementioned compounds were discussed.