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

Upasana Banerjee; Sujan K Sarkar; Jeanette A Krause; William L Karney; Manabu Abe; Anna D Gudmundsdottir

doi:10.1021/acs.orglett.0c02794

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

Org Lett. 2020 Oct 16;22(20):7885-7890. doi: 10.1021/acs.orglett.0c02794. Epub 2020 Sep 25.

Authors

Upasana Banerjee¹, Sujan K Sarkar¹, Jeanette A Krause¹, William L Karney², Manabu Abe³, Anna D Gudmundsdottir¹

Affiliations

¹ Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45220-0172, United States.
² Department of Chemistry, University of San Francisco, 2130 Fulton Street, San Francisco, California 94117, United States.
³ Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan.

PMID: 32975421
DOI: 10.1021/acs.orglett.0c02794

Abstract

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.