2017
DOI: 10.1021/acs.joc.7b01587
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Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

Abstract: In recent years, great synthetic potential of the photorearrangement of diarylethenes leading to naphthalene derivatives via a cascade process of photocyclization/[1,n]-H shift/cycloreversion has been demonstrated. In this work, first a multifaceted study of the influence of various factors on the efficiency of the photorearrangement of diarylethenes of furanone series containing benzene and oxazole derivatives as aryl residues has been carried out. The efficiency of this phototransformation (quantum yields) a… Show more

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Cited by 24 publications
(15 citation statements)
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“…Recently we used this assumption to calculate the quantum yields of photorearrangement of diarylethene 1 analogues: 2,3-diarylfuran-2(5H)-ones bearing different substituted benzenes. 18 Performing experiments in argon-saturated or oxygensaturated solutions results in the same changes in the UV spectrum as shown in Figure 1. The quantum yield of photolysis sufficiently depends on the concentration of dissolved oxygen (Figure 1, inset).…”
Section: Resultsmentioning
confidence: 68%
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“…Recently we used this assumption to calculate the quantum yields of photorearrangement of diarylethene 1 analogues: 2,3-diarylfuran-2(5H)-ones bearing different substituted benzenes. 18 Performing experiments in argon-saturated or oxygensaturated solutions results in the same changes in the UV spectrum as shown in Figure 1. The quantum yield of photolysis sufficiently depends on the concentration of dissolved oxygen (Figure 1, inset).…”
Section: Resultsmentioning
confidence: 68%
“…Curve 8 in Figure represents the spectrum of the product of skeletal rearrangement coinciding with that reported previously, which allows us to determine the quantum yield of the reaction. Recently we used this assumption to calculate the quantum yields of photorearrangement of diarylethene 1 analogues: 2,3-diarylfuran-2­(5 H )-ones bearing different substituted benzenes …”
Section: Resultsmentioning
confidence: 99%
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“…We commenced this study with the preparative synthesis of furanone DAEs 1a – c (Scheme S1). These diarylethenes were chosen since they can be conveniently synthesized in good yields from commercially available starting compounds and due to the high quantum yields of their photocyclization . Photocyclization of 1a – c under various conditions showed that the reaction pathway depended both on the kind of halogen substituent and solvent.…”
Section: Resultsmentioning
confidence: 99%
“…However, inert conditions were used in one of them, and no preparative synthesis was performed in another one (Scheme ). Efficient preparative reaction of cyclopentenone-based diarylethene 37c (Scheme ) in aerobic conditions became the starting point for a series of works , where the photorearrangement of diarylethenes 41 with cyclopentenone and furanone bridges was studied (Scheme ). Derivatives of benzene, naphthalene, and various heterocycles were used as the aromatic moieties whose nature determined the photolysis conditions.…”
Section: Blocking the Oxidation/elimination Processesmentioning
confidence: 99%