Reactivity of Tri‐<i>tert</i>‐butylazete

Abstract

The first kinetically stabilized azete, the title compound 1, is sensitive toward oxidation (→ formation of the dioxetane 2) and undergoes hydrolysis to the β-imino ketone 3. Sterically nondemanding cycloaddition partners such as cyclopentadiene or diazomethane (CH2N2) (→ formation of the adduct 4) attack at C-2/C-3, whereas those with bulky groups such as acetylenedicarboxylate esters or tert-butylphosphaacetylene (PCtBu) (→ formation of the bicyclic compound 5) react at N-1/C-4.