Aspect of the de novo carbonyl generated from a sterically regulated dioxetane

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Aryl-substituted bicyclic dioxetanes fused with an N-acylpyrrolidine were found to give syn/anti-rotamers which were individually isolated in pure form. These rotamers showed markedly different chemiluminescence properties, especially chemiluminescence efficiency, when treated with base in an aprotic polar solvent. The results suggested that the rotamers of dioxetane decomposed to initially give sterically different carbonyls. Crystalline benzoazolylphenol-substituted bicyclic dioxetanes possessing high-melting point were found to undergo chemiluminescent decomposition through which the crystalline state was sustained. The fresh crystalline carbonyl compound gave fluorescence and IR spectra and TA different from those of the authentic compound.