PHOTOCHEMISTRY OF NAPHTHYL AND PYRENYL AZIDES: CHEMICAL PROPERTIES OF THE TRANSIENT INTERMEDIATES PROBED BY LASER SPECTROSCOPY

Article abstract of DOI:10.1021/ja00330a033

The photochemistry of 1-naphthyl azide, 2-naphthyl azide, 1-pyrenyl azide, and 2-pyrenyl azide was examined in inert (benzene) and reactive (diethylamine) solvents.These studies employ a combination of product analysis, low-temperature spectroscopy, and laser-flash photolysis to reveal the chemical and physical properties of the highly reactive, short-lived intermediates formed in these reactions.In all cases two intermediates account for the observations.One of these is the triplet nitrene and the other is a ground-state singlet transient identified as an azirine.The relationship between these intermediates controls the chemical outcome of the reaction.