Benzenoid-quinoid tautomerism of azomethines and their structural analogs. 42. Synthesis, structures, and spectral-luminescence properties of 3-hydroxy-2-acetylbenzo[b]thiophene imines
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N-Aryl- and N-alkylimines of 3-hydroxy-2-acetylbenzo[b]-thiophene, the most stable isomeric form of which, according to the UV, IR, and 1H NMR spectra data, is the E-keto enamine structure, were synthesized. Irradiation of the aminovinyl ketones in the region of the long-wave absorption band causes thermally and photochemically reversible E⇄Z isomerization. 2-Aminoethylidene-3-(2H)-benzo[b]thiophenones have low-intensity fluorescence with a normal Stokesian shift, which is absent in solutions of their lithium and sodium salts.
KeywordsLithium Absorption Band Ketone Thiophene Structural Analog
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