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ISSUE 12

Year 2005, Month 12 (Section Full Articles, Page 2783)

Synthesis and properties of photoacylotropic (2Z )-2-(N-acyl-N-arylaminomethylidene)benzo[b]thiophen-3(2H)-ones with a chiral migrating group

V. P. Rybalkin (a), Ya. Yu. Vorob´eva (a), G. S. Borodkin (a), A. D. Dubonosov (b), A. V. Tsukanov (b), V. V. Tkachev (c), S. M. Aldoshin (c), V. A. Bren´ (a,b), and V. I. Minkina (b)

New photochromic (2Z )-2-(N-acyl0N-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.

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