Details

Autor(en) / Beteiligte

• Schulz, Marvin
• Christoffers, Jens

Titel

New macrocyclic bistriazolophanes with thioindigo chromophore

Ist Teil von

• Tetrahedron, 2013-01, Vol.69 (2), p.802-809

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

2013

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Bi(4-methoxycarbonyl-3-oxothiolan-2-ylidene) derivatives are prepared by oxidative dimerization of 4-oxotetrahydrothiophene-3-carboxylates with either TPAP–NMO or K3[Fe(CN)6]. The products are obtained as mixtures of four diastereoisomers due to (E)- or (Z)-configuration of the C–C double bond and relative syn- or anti-configuration of two stereocenters. The red compounds contain the prototype of the thioindigo chromophore. Their double bond configuration can be switched from (E) to (Z) by visible light. Two propargyl-functionalized thiolane monomers were clicked together by para-bis(azidoalkyl)benzene derivatives with [Cu(μ-OH)(tmeda)]2Cl2 as the catalyst, thus, the subsequent oxidative dimerization yielded macrocyclic triazolophane products with the bi(thiolan-2-ylidene) unit only in relative syn-configuration. [Display omitted]