35689-27-1Relevant academic research and scientific papers
Attractive and repulsive effects in the interactions between electron-rich and electron-deficient groups in peri-substituted naphthalenes
O'Leary, Jane,Bell, Paul C.,Wallis, John D.,Schweizer, W. Bernd
, p. 133 - 139 (2001)
The 1,5 Me2N...C(sp2) separations in a series of peri-substituted naphthalene derivatives are sensitive to the through-space electron-attracting power of the carbon-containing functional group, while the corresponding MeO...C(sp2) separations are relatively insensitive in accord with the different nucleophilicities of the two groups. These separations are a balance between a steric effect and a covalent interaction, and from a comparison of the Me2N...C and MeO...C distances for a given functional group it is proposed that the Me2N...C interaction has an attractive component if the Me2N...C separation is less than ～(MeO...C + 0.15) A, the latter factor arising from the greater size of the bonded nitrogen atom.
Palladium-Catalyzed Regiospecific peri- And ortho-C-H Oxygenations of Polyaromatic Rings Mediated by Tunable Directing Groups
Hu, Lihong,Jiang, Jing,Lin, Yaoyu,Ma, Congzhe,Song, Wanbin,Yuan, Dandan,Zhang, Yinan
supporting information, p. 279 - 284 (2021/01/13)
An efficient divergent approach of Pd-catalyzed C-H oxygenation of polyaromatic rings is described. Reversible directing groups enable regiospecific peri- and ortho-oxygenation to readily access a wide array of polyaromatic phenols without pre- and postmanipulation of directing groups. The systematic mechanistic investigation, including deuterium-labeling experiments, palladacycle trapping, and DFT calculations, reveals that the tunable ligand-assisted C-H bond cleavage played a crucial role during the reaction process.
Hydrogen peroxide oxidation of naphthalene derivatives catalyzed by poly (bis-1,2-diphenylene) diselenide
Giurg,Syper,Mlochowski
, p. 231 - 238 (2007/10/03)
Oxidation of 1- and 2-substituted naphthalenes (1) with 30% hydrogen peroxide in the presence of poly(bis-1,2-diphenylene) diselenide (PPDS) has been investigated. Depending on the substrate used trans-2-carboxycinnamic acid (2), and its isomer, (1-oxo-1,3-dihydroisobenzofuran-1-yl)acetic acid (3) or 2-naphthoic acid (4b) was a major product. Oxidation of hydroxynaphthalenes 1b and 1c is a convenient way to obtain trans-2-carboxy cinnamic acid (2) in almost quantitative yield. The mechanism of the reaction is postulated.
Selective synthesis of meso-naphthylporphyrins
Cammidge, Andrew N.,Oeztuerk, Orhan
, p. 7457 - 7464 (2007/10/03)
A series of novel meso-(8-substituted naphth-1-yl)porphyrins has been synthesized creating derivatives with a tight recognition environment above the porphyrin plane. The selective synthesis of single atropisomers is discussed. Condensation of bisnaphthaldehyde 12 with phenyldipyrromethane unexpectedly led to selective synthesis of the α,α-5,10-bridged isomer 14. A mechanism is proposed for this unusual scrambling, and alternative syntheses of α,α-5,15-bisnaphthylporphyrins are described. Synthesis of 5,15-analogues can be achieved by employing (pentafluorophenyl)-dipyrromethane or via presynthesis of a bis(dipyrromethane) derivative 22 (from bisnaphthaldehyde 12) and subsequent condensation with benzaldehyde.
Regioselectivity in the Reactions of Methoxydehydrobenzenes with Furans. Part 1. Reactions of 3-Methoxydehydrobenzene and 3-(Methoxycarbonyl)dehydrobenzene with 2-Substituted Furans.
Giles, Robin G. F.,Sargent, Melvyn V.,Sianipar, Hercules
, p. 1571 - 1579 (2007/10/02)
The isomer ratios for the cycloadducts obtained for the reaction of 3-methoxydehydrobenzene, generated from 2-amino-6-methoxybenzoic acid by aprotic diazotization, or from 2-bromo-3-methoxyphenyl toluene-p-sulphonate by treatment with butyllithium, and fo
Cycloadditions of Isoquinolinium Salts: Vinyl Sulfide Dienophiles for the Syntheses of 1-Naphthaldehydes and Tetralins
Gupta, Ram B.,Franck, Richard W.,Onan, Kay D.,Soll, Clifford E.
, p. 1097 - 1101 (2007/10/02)
Vinyl sulfides are used as dienophiles in the Bradsher cycloaddition reaction.Processing of the cycloadducts leads to either tetralins or naphthaldehydes.The tetralins are formed with high stereoselectivity.The configuration of the products is confirmed by an X-ray structure determination.Removal of sulfur from the tetralin products affords materials that are the equivalent of having used simple alkenes as dienophiles.
