Synthesis, structural characterization and photoisomerization of cyclic stilbenes

Oelgemöller, Michael, Frank, Rudolf, Lemmen, Peter, Lenoir, Dieter, Lex, Johann, and Inoue, Yoshihisa (2012) Synthesis, structural characterization and photoisomerization of cyclic stilbenes. Tetrahedron, 68 (21). pp. 4048-4056.

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Abstract

Six cyclic stilbene derivatives with hindered free rotation around the C(vinyl)–C(phenyl) single bond were synthesized by McMurry coupling. The torsion angles around the double and the single bond, and the C=C bond length were obtained for many of the compounds from their solid-state structures. The photochemical isomerization was subsequently investigated for all derivatives under various conditions. The parent 1-(1-tetralinylidene)tetralin underwent efficient oxidative electrocyclization. The 2,2,2',2'-tetramethylated analogue was resistant towards photooxidation, however, its cis-isomer thermally reisomerized to the more stable trans-isomer.

Item ID: 21674
Item Type: Article (Refereed Research - C1)
ISSN: 1464-5416
Date Deposited: 10 May 2012 05:46
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 25%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 75%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
Citation Count from Web of Science Web of Science 2
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