Isolation and reactivity of an unusually stable organoselenenyl azide

The stabilities of a series of isolated covalent selenium(II) azides such as [2-[1-(3,5-dimethylphenyl)-2-naphthyl]-4,5-dihydro-4,4-dimethyloxazole]selenium azide (2a), [2-(4,4-dimethyl-2-oxazolinyl)phenyl]selenenyl azide (3a), [o-(2,6-diisopropylphenyl-iminomethinyl)phenyl]selenenyl azide (4a), [o-(R)-(methylbenzyliminomethinyl)phenyl]selenenyl azide (5a) and o-formylphenylselenenyl azide (6a) are rationalized; also the reactivity of first room temperature stable azide (2a) toward 1,3-cycloaddition has been explored.