24776-44-1

Upstream product

• 607-55-6 α-naphthyl benzoate 
• 24776-45-2 1-benzoyl-4-methoxynaphthalene 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 5328-01-8 1-ethoxynaphthalene 
• 98-88-4 benzoyl chloride 
• 280763-60-2 1-[2-(2-phenyl-1-ethynyl)phenyl]-2-propyn-1-one 
• 90-15-3 α-naphthol 
• 98-07-7 Benzotrichlorid 

Downstream Products

• 124121-74-0 5-benzoyl-dinaphtho[1,2-b;2',3'-d]furan-7,12-quinone 
• 72261-62-2 4-benzylnaphthalene-1,2-dione 
• 108054-95-1 2-Hydroxy-4-[1-phenyl-meth-(E)-ylidene]-4H-naphthalen-1-one 
• 108055-01-2 C₁₇H₁₁⁽²⁾HO₂ 
• 1226896-59-8 (R)-4'-benzoyl-3,4-dihydro-1'H,5H-spiro[furan-2,2'-naphthalene]-1',5-dione 
• 1226896-50-9 3-(4-benzoyl-1-hydroxynaphthalen-2-yl)propanoic acid 
• 90-15-3 α-naphthol 
• 65-85-0 benzoic acid 
• 94866-78-1 1-(4-Benzoyl-1-naphthoxy)-butanon-⁽²⁾ 
• 28178-96-3 4-(phenylmethyl)-1-naphthalenol 

Relevant academic research and scientific papers

An Unusual Conversion of 2-(Alkynonyl)Alkynylbenzenes to Isocoumarins by a Retro-Favorskii-like Degradation

We report the discovery of an anomalous reaction of 2-(alkynonyl)alkynylbenzenes under AgI catalysis for the selective formation of isocoumarins. This reaction is previously undocumented for 2-(alkynonyl)alkynylbenzenes in terms of the reaction mechanism and the product formed. Water (H2O18) labeling studies suggested a possible mechanistic pathway in which the initial formation of a pyrylium ion is followed by hydrative dealkynylation, that is, water incorporation and alkyne expulsion, similar to a retro-Favorskii reaction.

Asymmetric Oxidative Cycloetherification of Naphtholic Alcohols

The catalytic, enantioselective oxidative cyclization of naphthol-derived carboxylic acids mediated by chiral hypervalent iodine reagents has been studied extensively in the recent past, but analogous reactions of non-carboxylic substrates are yet unknown. This paper describes a catalytic, enantioselective, hypervalent iodine-promoted oxidative cycloetherification reaction of naphtholic alcohols. The new process relies on a variant of the Uyanik–Ishihara catalyst, in which the stereogenic centers have been relocated closer to the iodine atom. The new catalyst design affords optical yields comparable to those available with Uyanik–Ishihara iodides, but chemical yields are sensibly higher, at least with the tests substrates. An even more problematic reaction is the catalytic, enantioselective oxidative cyclization of naphtholic sulfonamides. In this case, the new catalyst affords significantly higher optical inductions than Uyanik–Ishihara iodides. The kinetic resolution of particular naphtholic alcohols is demonstrated. The absolute configuration of a numver of enantioenriched compounds obtained in this study was ascertained by X-ray diffractometry.

Synthesis of spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers via 1,6-conjugate addition induced dearomatization of para-quinone methides

An efficient one-pot approach for the synthesis of spiro[2.5]octa-4,7-dien-6-ones by employing para-quinone methides has been developed. The reaction proceeded smoothly in high yields under mild conditions without the use of metals. Moreover, all products obtained herein contained two or three consecutive quaternary centers.

Photo-Fries reaction in water made selective with a capsule

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 ion exchanged nafion as a confining medium for photochemical reactions

Methanol-swollen Nafion beads were used as microreactors to control the photochemical reaction pathways. Product selectivity in three unimolecular reactions, namely, the photo-Fries rearrangement of naphthyl esters, Norrish Type I reaction of 1-phenyl-3-p-tolyl-propan-2-one and Norrish Type I and Type II reactions of benzoin alkyl ethers were examined. The influence of cations over the photodimerization of acenaphthylene and cross-photodimerization between acenaphthylene and N-benzyl maleimide included within Nafion were also examined. The photochemical behaviors of the above substrates were significantly altered within Nafion compared with their solution photochemistry. Of particular interest, the product distributions were found to depend on the counter cations of Nafion.

Amphiphilic homopolymer as a reaction medium in water: Product selectivity within polymeric nanopockets

A styrene-based water-soluble polymer has been explored for its use as a host for lipophilic substrates in aqueous medium. Unimolecular reactions, namely, photo-Fries rearrangement of naphthyl esters, α-cleavage reaction of 1-phenyl-3-p-tolyl-propan-2-one, and Norrish type I and type II reactions of benzoin alkyl ethers were examined. We find that the hydrophobic domains generated by the polymer not only restrict the mobility of the radicals but also modestly incarcerate the substrate, intermediates, and products during the time scale of the reactions. Comparative studies of the same photoreactions in micelles formed from small molecule surfactants and an amphiphilic diblock copolymer demonstrate that the styrene-based water-soluble polymer aggregates in aqueous medium offer better selectivity.

Facile synthesis of regio-isomeric naphthofurans and benzodifurans

Naphtho[1,2-b]furans 1a-f, naphtho[2,1-b]furans 2a-f, benzo[1,2-b:5,4- b′]difurans 3a-b, benzo[1,2-b:4,5-b′]difurans 4a-b, and benzo[1,2-b:4,3-b′]difurans 5a-b were synthesized by base-catalyzed cyclization reaction of the corresponding o-alkoxybenzoylarene derivatives. The o-alkoxybenzoylarenes were obtained from the etherification reaction of the o-hydroxybenzoylarenes, which were prepared either by the reaction of methoxyarenes with benzoyl chloride in the presence of aluminum chloride or by photo-Fries rearrangement of aryl benzoates. Graphical Abstract.

Water-soluble dendrimers as photochemical reaction media: Chemical behavior of singlet and triplet radical pairs inside dendritic reaction cavities

Water-soluble poly(alkyl aryl ether) dendrimers have been explored for their use as hosts of organic substrates in aqueous media. Prototypical photoreactions, namely, photo-Fries reaction of (a) 1-naphthyl benzoate and (b) 1-naphthyl phenyl ester and α-cleavage reaction of (a) dibenzyl ketones and (b) benzoin alkyl ethers, have been examined. We find that a dendritic microenvironment not only restricts the mobility of radical intermediates but also rigidly encapsulates the substrate, intermediates, and products from "leaking" to the bulk environment. Comparative studies of the same photoreactions in micellar media demonstrate that dendritic media offer much better constrainment than the micelles.

Improvement of Selectivity in the Fries Rearrangement and Direct Acylation Reactions by Means of P2O5/SiO2 Under Microwave Irradiation in Solvent-Free Media

P2O5/SiO2 was found to be an efficient new reagent for the Fries rearrangement of acyloxy benzene or naphthalene derivatives and the direct acylation reactions of phenol and naphthol derivatives with carboxylic acids. The reactions proceeded smoothly in the solid state and are highly selective methods for the preparation of the ortho isomers of hydroxyaryl ketones. Microwave irradiation improved the conversion yield to 85-100 percent and the high ortho-regioselectivity of these reactions provides an efficient and versatile procedure for obtaining o-hydroxyaryl ketones in 47-98 percent yield.

Effect of cyclodextrin complexation on photo-fries rearrangement of naphthyl esters

Photolysis of β-cyclodextrin inclusion complexes of 1- and 2-naphthyl esters (acetates and benzoates) in aqueous medium, results in rearrangement to give one isomer of acylnaphthol in excess, whereas the solid state irradiation of the cyclodextrin complexes yields selectively one isomer. In addition, formation of cleavage product is totally suppressed. This remarkable selectivity is attributed to specific modes of the complexation of the esters into the β-CD cavity.