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The Mechanism of Photoinduced Acylation of Amines by N-Acyl-5,7-dinitroindoline as Determined by Time-Resolved Infrared Spectroscopy

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journal contribution
posted on 07.07.2005, 00:00 by Andrew D. Cohen, Céline Helgen, Christian G. Bochet, John P. Toscano
The photochemistry of N-acyl-5,7-dinitroindoline (1) was studied in acetonitrile using nanosecond time-resolved infrared (TRIR) spectroscopy. Upon photolysis, two nearly but not completely overlapping sets of transient IR bands are observed that are assigned to two non-interconvertible conformers of mixed acetic nitronic anhydride 7. While syn-7 reverts rapidly to 1, anti-7 is long-lived and is able to acylate amines. Results of density functional theory calculations support conclusions based on experimental TRIR data.