Abstract: Two stereoisomeric di-tert-butylbis (bicyclo [3.3. l] non-9-ylidenes)(anti-2 and syn- 2) and related hindered olefins were synthesized, and their reactivities and stereochemistries in various dioxetane formations were evaluated. Whereas the singlet oxygenation of a series of three closely related olefins, 1, 3, and 4, gave the corresponding dioxetanes in almost the same reactivity, in the electrode-catalyzed oxygenation the ...