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α-Cleavage of 2,2-Diazido-2,3-dihydroinden-1-one in Solution and Cryogenic Matrices

https://doi.org/10.1021/acs.joc.4c00499

James, Brandi; Sriyarathne, H. Dushanee; Banerjee, Upasana; Henarath Mohottige, Wandana K.; Crabtree, Ben; León, Aliz; Hong, Miao; Tariq, Javeria; Alhayani, Taha; Abe, Manabu; et al (May 2024, The Journal of Organic Chemistry)

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Photo-Uncaging by C(sp ³ )–C(sp ³ ) Bond Cleavage Restores β-Lapachone Activity

https://doi.org/10.1021/jacs.3c00398

Kaye, Esther G; Mirabi, Bijan; Lopez-Miranda, Ivonne R; Dissanayake, Komadhie C; Banerjee, Upasana; Austin, Madelyn; Lautens, Mark; Winter, Arthur H; Beharry, Andrew A (June 2023, Journal of the American Chemical Society)

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

https://doi.org/10.1021/acs.orglett.0c02794

Banerjee, Upasana; Sarkar, Sujan K.; Krause, Jeanette A.; Karney, William L.; Abe, Manabu; Gudmundsdottir, Anna D. (October 2020, Organic Letters)

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Photolysis of 5-Azido-3-Phenylisoxazole at Cryogenic Temperature: Formation and Direct Detection of a Nitrosoalkene

https://doi.org/10.3390/molecules25030543

Banerjee, Upasana; Karney, William L.; Ault, Bruce S.; Gudmundsdottir, Anna D. (February 2020, Molecules)

To enhance the versatility of organic azides in organic synthesis, a better understanding of their photochemistry is required. Herein, the photoreactivity of azidoisoxazole 1 was characterized in cryogenic matrices with IR and UV-Vis absorption spectroscopy. The irradiation (λ = 254 nm) of azidoisoxazole 1 in an argon matrix at 13 K and in glassy 2-methyltetrahydrofuran (mTHF) at 77 K yielded nitrosoalkene 3. Density functional theory (DFT) and complete active space self-consistent field (CASSCF) calculations were used to aid the characterization of nitrosoalkene 3 and to support the proposed mechanism for its formation. It is likely that nitrosoalkene 3 is formed from the singlet excited state of azidoisoxazole 1 via a concerted mechanism or from cleavage of an intermediate singlet nitrene that does not undergo efficient intersystem crossing to its triplet configuration.
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