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Photoinduced α‑Cleavage of 2‑Azido-2-phenyl-1,3-indandione at Cryogenic Temperatures

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journal contribution
posted on 25.09.2020, 14:38 authored by Upasana Banerjee, Sujan K. Sarkar, Jeanette A. Krause, William L. Karney, Manabu Abe, Anna D. Gudmundsdottir
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.