Base-induced decomposition of dioxetanes bearing a 3-hydroxyphenyl moiety substituted with a proton-donating group at the 4-position: effect of intramolecular hydrogen bonding on decomposition rate and chemiluminescence efficiency

Bicyclic dioxetanes bearing a 3-hydroxyphenyl moiety substituted with an amidomethyl group (3a–c) or a hydroxymethyl group (4) were synthesized. On treatment with tetrabutylammonium fluoride in CH3CN, they decomposed rapidly with accompanying emission of blue light. Their decomposition rates and chemiluminescence efficiencies were found to be affected by the intramolecular hydrogen bonding between the phenoxy anion and the adjacent proton-donating group.