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Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-07-22 , DOI: 10.3762/bjoc.16.149
Vladimir P Rybalkin 1 , Sofiya Yu Zmeeva 2 , Lidiya L Popova 2 , Valerii V Tkachev 3 , Andrey N Utenyshev 3 , Olga Yu Karlutova 2 , Alexander D Dubonosov 1 , Vladimir A Bren 2 , Sergey M Aldoshin 3 , Vladimir I Minkin 2
Affiliation  

2-Benzo[b]thienyl fulgides and fulgimides containing bulky diphenylmethylene substituents were synthesized in the form of their ring-opened E- or Z-isomers. In contrast to the majority of known fulgides/fulgimides, that form colored ring-closed structures under UV irradiation, the obtained compounds undergo an irreversible transformation leading to decoloration of their solutions. This rearrangement with the formation of the dihydronaphthalene core appeared to be by 2–3 orders of magnitude more efficient than for the known diphenylmethylene(aryl(hetaryl))fulgides. The molecular structures of E- and Z-isomers and of products of the photoinduced rearrangement completed by 1,5-H shift reaction, 3a,4-dihydronaphtho[2,3-c]furans(pyrroles) C, were established based on the data of 1H and 13C NMR spectroscopy and X-ray diffraction studies.

中文翻译:

二苯基亚甲基(2-苯并[b]噻吩基)全氟化合物和全氟酰亚胺的合成和高效光诱导的重排。

以其开环的E-Z-异构体的形式合成了2-苯并[ b ]噻吩基单酸酯和含有庞大的二苯基亚甲基取代基的单酰亚胺。与在紫外线辐射下形成有色的闭环结构的大多数已知的三卤化物/三卤甲烷相反,所获得的化合物经历不可逆的转化,导致其溶液脱色。与形成二氢萘核相比,这种重排效率要比已知的二苯基亚甲基(芳基(杂芳基))全氟化合物高2-3个数量级。E-Z-的分子结构基于1 H和13 C NMR光谱数据,建立了通过1,5-H移位反应完成的光致重排异构体和3a,4-二氢萘并[2,3- c ]呋喃(吡咯)C的异构体和产物。和X射线衍射研究。
更新日期:2020-07-22
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