Refernces
10.1016/j.tetlet.2006.04.097
The research focuses on the synthesis of substituted 3-furan-2(5H)-ones, which are structural motifs found in numerous bioactive natural products. The methodology involves a Diels–Alder sequence using anthracene and maleic anhydride to form a lactone, which upon deprotonation and electrophilic quenching, yields α-substituted lactones. Key reactants include anthracene, maleic anhydride, sodium borohydride, and various electrophiles such as methyl iodide, allyl iodide, butenyl bromide, benzyl bromide, tributyltin chloride, diethyl chlorophosphate, and chlorotrimethylsilane. The experiments utilize techniques like flash vacuum pyrolysis (FVP) to convert alkylated lactones into 3-substituted furan-2(5H)-ones. The study also explores the challenges and limitations of using cyclopentadiene in such reactions and proposes an alternative route to overcome these issues. Analytical techniques such as 13C NMR and IR spectroscopy were employed to confirm the structure and successful functionalization of the synthesized compounds.
10.1021/ol302742g
The research aims to modulate the photoisomerization efficiency of N,C-chelate boryl chromophores, which are photoresponsive materials with potential applications in molecular electronics, optical data storage, molecular switching, and logic technologies. The study focuses on understanding the role of triplet acceptors, such as naphthalene, pyrene, and anthracene, in controlling the photoisomerization process and establishing the involvement of a photoactive triplet state in the isomerization of these photochromic compounds. The researchers synthesized a series of compounds (1-3) incorporating a photochromic boryl chromophore and different aromatic acceptors with varying triplet energies. They found that the photoisomerization quantum yield can be modulated by controlling the triplet energy of the acceptor, with compounds 1 and 2 undergoing quantitative conversion to their dark isomers with different quantum yields, while compound 3 showed suppressed isomerization. The study concluded that the photoisomerization of N,C-chelate dimesitylboranes likely proceeds via a triplet state, and the photoreactivity can be effectively modulated by controlling the triplet-triplet energy gap between the photochromic unit and the triplet acceptor chromophore. This finding has significant implications for the design of photochromic N,C-chelate boron compounds, suggesting that the photoisomerization can be sensitized or quenched using appropriate triplet sensitizers or acceptors.
10.1021/jo00343a001
The research focuses on the molten salt catalyzed transfer hydrogenation of polycyclic aromatic hydrocarbons, specifically the selective hydrogenation of anthracene and naphthacene by tetralin in the presence of molten antimony trichloride (SbCl3) as a catalyst at 80°C. The study aims to understand the redox-initiated ionic mechanism involving the arene radical cation and the 1-tetralyl cation as key intermediates in these transfer hydrogenation reactions. The conclusions drawn from the research indicate that anthracene and naphthacene are selectively hydrogenated to 9,10-dihydroanthracene and 5,12-dihydronaphthacene, respectively, without forming naphthalene, and instead, the dehydrogenated tetralin reacts with itself and unreacted arene to give alkylated products. The chemicals used in this process include anthracene, naphthacene, tetralin, and molten SbCl3, with additional compounds such as phenanthrene, pyrene, and perylene being tested under similar conditions to understand their reactivity patterns.
10.1039/c3sc50643f
The study presents a method for synthesizing cyclobutane lignans and their analogs using photoinduced electron transfer. Key chemicals include oxygenated alkenes, which are used to form terminal or substituted cyclobutane adducts with complete regiocontrol and trans stereochemistry. The aromatic electron relay (ER), such as anthracene or naphthalene, is crucial for minimizing competing cycloreversion. The photooxidant 2,4,6-tris(4-methoxyphenyl)pyrylium tetrafluoroborate (p-OMeTPT) is used to excite the system and facilitate the oxidation of the alkene substrate by the ER, which then forms a cation radical capable of oxidizing the alkene. This method has been successfully applied to synthesize natural products like magnosalin and pellucidin A. The study also explores the role of the ER in preventing cycloreversion and polymerization, highlighting its importance in achieving higher yields and selectivity in the cyclobutane synthesis.
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