1,2-Dioxetane

When in basic solution, this compound converts to the imidazolate, which reacts with oxygen to eventually give the 1,2-dioxetane.

[1] In the 1960s, 1,2-dioxetane were demonstrated as intermediates in the reactions responsible for the bioluminescence in fireflies, glow-worms, and other luminescent creatures.

[3] In 1968 the first example of a stable dioxetane derivative was made at the University of Alberta in Edmonton: 3,3,4-trimethyl-1,2-dioxetane, prepared as a yellow solution in benzene.

When heated to 333 K, it decomposed smoothly (rather than explosively, as many peroxides do) to acetone and acetaldehyde with the emission of pale blue light.

[4] The second example of a dioxetane derivative was made shortly after: the symmetrical compound 3,3,4,4-tetramethyl-1,2-dioxetane, obtained as pale yellow crystals that sublimed even when kept in the refrigerator.

Steps leading up to chemiluminescence of lophine.