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Open Access Green as soon as Postprint is submitted to ZB.
Synthesis, structural characterization and photoisomerization of cyclic stilbenes.
Tetrahedron 68, 4048-4056 (2012)
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 re-isomerized to the more stable trans-isomer.
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Publication type
Article: Journal article
Document type
Scientific Article
Keywords
Mcmurry Coupling ; Stilbene ; Photochemistry ; Photoisomerization ; Dihydrophenanthrene; LOW-VALENT TITANIUM; STERICALLY-HINDERED OLEFINS; CIS-TRANS ISOMERIZATION; MOLECULAR-STRUCTURE; CRYSTAL-STRUCTURE; CONFORMATIONAL-ANALYSIS; COUPLING REACTIONS; STIFF-STILBENES; BOND TORSION; GAS-PHASE
ISSN (print) / ISBN
0040-4020
e-ISSN
1464-5416
Journal
Tetrahedron
Quellenangaben
Volume: 68,
Issue: 21,
Pages: 4048-4056
Publisher
Elsevier
Non-patent literature
Publications
Reviewing status
Peer reviewed
Institute(s)
PPM-MEX-Molecular EXposomics (MEX)