Photoinduced Acylotropic Rearrangement of Crown-Containing 2-[N-Acetyl-N-(4-aminobenzo-15-crown-5)methylene]-2,3-dihydrobenzo[b]thiophen-3-one |
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Authors: | V. P. Rybalkin A. D. Dubonosov E. N. Shepelenko L. L. Popova V. A. Bren'' V. I. Minkin |
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Affiliation: | (1) Research Institute of Physical and Organic Chemistry, Rostov State University, pr. Stachki 194/2, Rostov-on-Don, 344090, Russia |
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Abstract: | 2-N-(4-Aminobenzo-15-crown-5)methylene-2,3-dihydrobenzo[b]thiophen-3-one and its acetyl derivative were synthesized. Their treatment with lithium, sodium, or potassium iodide in acetonitrile solution leads to formation of the corresponding crown-metal complexes. Irradiation of the acylated compounds at 436 nm induces NO migration of the acetyl group to give O-acyl isomer which is characterized by a considerable blue shift of the long-wave absorption band ( = 70 nm). The quantum yields of the photo- induced acylotropic reaction for the free ligand and its complexes with alkali metal cations change in the series: L > K+ > Na+ > Li+. |
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