92545-53-4

Upstream product

• 611-71-2 MANDELIC ACID 
• 65425-11-8 5,5′-dimethyl-3,3′-diphenyl-3H,3′H[3,3′]-bibenzofuranyl-2,2′-dione 
• 67-56-1 methanol 
• 39531-24-3 5-methyl-3-phenyl-1-benzofuran-2(3H)-one 

Relevant academic research and scientific papers

Recyclable nickel-catalyzed C-H/O-H dual functionalization of phenols with mandelic acids for the synthesis of 3-aryl benzofuran-2(3: H)-ones under solvent-free conditions

Herein, we developed a protocol for the efficient synthesis of 3-aryl benzofuran-2(3H)-ones under solvent-free conditions from phenols and mandelic acids using Ni(OTf)2 as a catalyst. A diverse range of mandelic acids and phenols undergo C-H/O-

Catalytic Oxidation of 3-Arylbenzofuran-2(3 H)-ones with PCC-H5IO6: Syntheses of 3-Aryl-3-hydroxy/3-amido-3-arylbenzofuran-2(3 H)-ones

A pyridinium chlorochromate (PCC)-mediated facile oxidative dimerization of 3-arylbenzofuran-2-ones at ambient temperature was developed which undergo oxidative cleavage to 3-aryl-3-hydroxy-benzofuran-2-ones with PCC at elevated temperatures. Finally, dir

Photochemical and Thermal Transformations of 2(3H)-Furanones and Bis(benzofuranones). A Laser Flash Photolysis study

Transformations of the 2(3H)-furanones 1-4 and bis(benzofuranones) 16-18 under steady-state photolysis and thermolysis are reported.Irradiation of 1 in benzene gives a mixture of the decarbonylated product 5 (62percent) and the cyclized phenanthrene derivative 10 (15percent).Similar results were obtained when the photolysis of 1 was carried out in methanol and acetone.Irradiation of 2 in benzene and methanol gave exclusively the decarbonylation product 6, whereas, in acetone, a mixture of the rearranged lactone 13 and and its cyclized product, 15, was obtained.Irradiation of both 3 and 4 gave the cyclized products 11 and 12, respectively.In contrast, the photolysis of the bis(benzofuranone) 16 in cyclohexane gave 3-phenylbenzo-2-(3H)-furanone (25), whereas the photolysis in methanol led to a mixture of methyl α-(2-hydroxyphenyl)phenylacetate (34) and 3-hydroxy-3-phenylbenzo-2(3H)-furanone (31).Similar results were obtained in the irradiation of 17 and 18.Neat thermolysis of furanones 1-3 at 350-450 deg C gave the decarbonylated products 5, 6, and 37 in 36-80 percent yields, whereas furanone 4 underwent facile isomerization to 5-benzyl-3,4,5-triphenyl-2(5H)-furanone (38), upon refluxing in diphenyl ether (ca. 255 deg C).Heating of bis(benzofuranones) 16-18 in refluxing cumene (ca. 150 deg C) gave the corresponding furanones 25-27 in 62-68 percent yields.Laser flash photolysis of furanones 1-4 at 248 and 337 nm leads to absorption spectral changes that can be explained in terms of singlet-mediated decarbonylation (φ = 0.3 for 2 in methanol, λex = 248 nm) and cyclization, i.e., dihydrophenanthrene formation (φ = 0.1-0.5 for 1, 3, and 4 in benzene and methanol, λex = 337 nm).The triplets of the furanones generated under energy-transfer sensitization by benzophenone in benzene are relatively long lived (r = 1.2-12 μs) and exhibit absorption maxima at 330-370 nm (εmax = (11-14) * 103 M-1 cm-1); these spectral and kinetic features appear to be characteristic of the styrene and cis-stilbene chromophores, constrained into planar configurations.Upon laser flash photolysis at 248 nm in methanol, bis(benzofuranones) 16-18 undergo facile fragmentation to the corresponding radicals 19-21, characterized by sharp and intense absorption maxima at ca. 330 nm, in addition to broad and weak absorption band systems at 500-600 nm; these radical species are the primary intermediates implicated in the formation of various final products in the course of steady-state photolysis of 16-18 under different conditions.