Photoinduced α-Cleavage of 2-Azido-2-phenyl-1,3-indandione at Cryogenic Temperatures
2020
Banerjee, Upasana | Sarkar, Sujan K. | Krause, Jeanette A. | Karney, William L. | Abe, Manabu | Gudmundsdottir, Anna D.
To expand the utility of α-cleavage at cryogenic temperatures, we investigated the photoreactivity of 2-azido-2-phenyl-1,3-indandione (1). EPR spectroscopy revealed that irradiating 1 in 2-methyltetrahydrofuran (mTHF) matrices forms alkylnitrene ³2, which has zero-field splitting parameters (D/hc = 1.5837 cm–¹; E/hc = 0.0039 cm–¹) typical of an alkylnitrene. IR spectroscopy demonstrated that irradiating 1 in argon matrices results in the concurrent formation of ³2, imine 3, benzocyclobutenedione 4, and benzonitrile 5.
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