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Trans-3-(2-tert-butylcyclopropyl)-3H-diazirine was decomposed both thermally and photochemically to give the anticipated ring-expanded 3-tert- butylcyclobutene product, along with azine and products of trapping by solvent, In the presence of tetramethylethylene (TME), a bicyclopropane adduct was formed The yield of 3-tert-butylcyclobutene product, however, is only very slightly (0-7%) decreased upon increasing the concentration of TME. Thus there must be two product-forming pathways. One pathway is a relaxed carbene intermediate, the second with the excited singlet state of the diazirine precursor. It is posited that upon activation diazirines open to form a diazirinyl diradical which undergoes the following processes: a)ring closure to reform the diazirine, b)formation of the linear diazo compound, c)cleavage to form carbene and dinitrogen, d)rearrangement to cyclobutene in concert with nitrogen extrusion.

Photochemical rearrangements of diazirines and thermal rearrangements of carbenes