2491-34-1Relevant articles and documents
Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarinviaa TsOH-mediated tandem reaction
Li, Chenyu,Liang, Yong,Ma, Zhishuang,Wang, Ding,Wang, Nana,Wang, Tao,Zhang, Zunting
supporting information, p. 10369 - 10372 (2020/09/16)
A concise and efficient method for the synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin using available 1-(2-hydroxyphenyl)-2-phenylethanone and Meldrum's acid has been developed. This transformation involved a tandem aldol reaction/lactonization/Friedel-Crafts reaction to form a lactone ring and a benzene ring. It showed high atom economy with water and acetone as the byproducts. Mechanism studies demonstrated two roles of Meldrum's acid: (i) as the reagent for the tandem reaction, and (ii) as the catalyst for the Friedel-Crafts reaction. Moreover, the hydroxyl group of 7-hydroxy-6H-naphtho[2,3-c]coumarin was further functionalized efficiently by arylethynyl, aryl, and cyano groups to furnish D-π-A compounds with excellent fluorescence emissions (ΦF= 0.14-0.78).
Selectivity in the photo-Fries reaction of phenyl phenylacetates included in a nation membrane
Tung, Chen-Ho,Xu, Xiao-He
, p. 127 - 130 (2007/10/03)
Photoirradiation of phenyl phenylacetates included within a Nafion membrane exclusively resulted in ortho-hydroxyphenones, thus achieving high selectivity in the photo-Fries reaction.
Photochemistry of phenyl phenylacetates adsorbed on pentasil and faujasite zeolites
Tung, Chen-Ho,Ying, Yun-Ming
, p. 1319 - 1322 (2007/10/03)
The photochemistry of phenyl phenylacetate 1, p-tolyl phenylacetate 2, o-tolyl phenylacetate 3 and phenyl o-tolylacetate 4 was investigated both in homogeneous solution and adsorbed on ZSM-5 and NaY zeolites.Photolyses of these esters in acetonitrile result in photo-Fries rearrangement products, phenols and diphenylethane as well as phenyl benzyl ethers.In contrast, photolyses of these esters adsorbed on NaY zeolite only give the ortho Fries rearrangemnt products.On the other hand, the photochemical reaction of 1 and 2 adsorbed on ZSM-5 zeolite only produces toluene and phenols, while under identical conditions the photochemical products for 3 and 4 are the Fries rearrangement and decarbonylation products. the product distributions for these esters adsorbed both on ZSM-5 and NaY zeolites are different from those for dibenzyl ketones as reported in the literature.All of these observations are interpreted in terms of (a) the size and shape sorption selectivity of ZSM-5 zeolite, (b) restriction of duffusional and rotational mobility of the radical pair imposed by the zeolite surface and (c) the multiplicity of the excited state responsible for the homolytic bond cleavage.