3669-44-1Relevant academic research and scientific papers
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
Ytterbium triflate catalysed Friedel-Crafts reaction using carboxylic acids as acylating reagents under solvent-free conditions
Jin, Can,Li, Jie,Su, Weike
experimental part, p. 607 - 611 (2011/02/26)
The Friedel-Crafts acylation of 1-naphthol and phenol derivatives with carboxylic acids were investigated by using a catalytic amount of metal-triflate, in particular Yb(OTf)3, under solvent-free conditions. Both aliphatic and aromatic carboxylic acids reacted easily to afford the corresponding hydroxyaryl ketones.
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.
Alkali metal ion controlled product selectivity during photorearrangements of 1-naphthyl phenyl acylates and dibenzyl ketones within zeolites
Warrier,Kaanumalle, Lakshmi S.,Ramamurthy
, p. 620 - 631 (2007/10/03)
Photochemical behaviors of 1-naphthyl phenyl acylates and dibenzyl ketones included in zeolites have been compared. 1-Naphthyl phenyl acylates while in solution produce eight photoproducts; within NaY it gives a single product. The selectivity is attributed to the restriction brought on the mobility of the primary radical pair by the alkali metal ions present in zeolites. Photochemistry of dibenzyl ketones within NaY reveals that the intersystem crossing in caged radical pairs could be influenced by the heavy alkali metal ions. Structures of complexes among Li+ ion and the guest 1-naphthyl phenyl acetates and dibenzyl ketone computed at the B3LYP level have been useful to understand the origin of the observed product selectivity within zeolites.
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.
