Synthesis and properties of photoacylotropic (2Z)-2-(N-acyl-N-arylaminomethylidene)benzo[b]thiophen-3(2H)-ones with a chiral migrating group |
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| Authors: | V. P. Rybalkin, Ya. Yu. Vorob&# eva, G. S. Borodkin, A. D. Dubonosov, A. V. Tsukanov, V. V. Tkachev, S. M. Aldoshin, V. A. Bren&# V. I. Minkin |
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| Affiliation: | (1) Institute of Physical and Organic Chemistry, Rostov State University, 194/2 prosp. Stachki, 344090 Rostov-on-Don, Russian Federation;(2) Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova, 344006 Rostov-on-Don, Russian Federation;(3) Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432 Chernogolovka, Moscow Region, Russian Federation |
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| Abstract: | New photochromic (2Z)-2-(N-acyl-N-arylaminomethylidene)benzo[b]thiophen-3(2H)-ones containing L-amino acid derivatives as migrating groups were synthesized. Light irradiation of their solutions at 436 nm leads to the photoinduced acylotropic rearrangement N → O accompanied by migration of the chiral fragment. The bulky N-acyl group causes steric strain thus destabilizing the amide form of compounds and facilitating the photorearrangement. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2690–2696, December, 2005. |
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| Keywords: | benzo[b]thiophene ketoenamine photochromic compounds chirality |
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