3669-44-1Relevant articles and documents
Ac2O-Mediated Dearylacetylative Dimerization of 2-Arylacetyl-1-naphthols: Synthesis of Naphtho[1,2-b]furan-3-ones
Chang, Meng-Yang,Chen, Kuan-Ting,Chen, Shin-Mei,Hsiao, Yu-Ting
, p. 3605 - 3616 (2020/03/23)
A novel and efficient route for the synthesis of 2-Aryl-2-naphthyl naphtho[1,2-b]furan-3-ones is described via NaH/Ac2O-mediated dearylacetylative dimerization of 2-Arylacetyl-1-naphthols in refluxing THF under open-flask conditions. A plausibl
Photo-Fries reaction in water made selective with a capsule
Kaanumalle, Lakshmi S.,Gibb, Corinne L. D.,Gibb, Bruce C.,Ramamurthy
, p. 236 - 238 (2008/03/14)
The water soluble capsule formed by a deep cavity cavitand with eight carboxylic acid groups controls product distribution during photo-Fries rearrangement of naphthyl esters in water by restricting the mobility of primary singlet radical pair. The Royal Society of Chemistry.
Mediation of photochemical reactions of 1-naphthyl phenylacylates by polyolefin films. A 'radical clock' to measure rates of radical-pair cage recombinations in 'viscous space'
Gu, Weiqiang,Weiss, Richard G.
, p. 6913 - 6925 (2007/10/03)
The fates of phenylacyl/1-naphthoxy singlet radical pairs generated upon irradiation of 1-naphthyl phenylacetate (1a) and 1-naphthyl 2-phenylpropanoate (1b) in three unstretched and stretched polyethylene films and isotactic and syndiotactic polypropylene films have been investigated. From dynamic fluorescence measurements the primary locus of reactions by 1 is within amorphous regions of the films. The reaction cages afforded by these media inhibit escape of the radical pairs and mediate their reorientational motions leading to photo-Fries and related products. In essence, the cages act as stiff-walled templates. In addition, a method is described to measure the rate constants for the singlet radical pairs. Thus, the rate constants (leading to the keto precursors) of the 2-phenylacyl-1-naphthols from the radical pairs of 1 (> 108 s-1) are >6 times the rate constants for the 4-isomers. Film stretching increases this selectivity but there is no obvious correlation between the rate of the in-cage radical pair recombinations and macroscopic polymer, properties such as degree of crystallinity and frequency of branched chains. By contrast, formation of (the keto precursors of) 2-benzylic-1-naphthols (from in-cage recombinations after phenylacyl decarbonylation) is slower than for the 4-benzyl-1-naphthols. (C) 2000 Elsevier Science Ltd.