Naphthalene Series Research Articles

Capture du paradiméthoxyorthoquinodiméthane: synthèses de quinones et d'un intermédiaire de la daunomycinone

New para-dimethoxyl and para-diacetoxy derivatives in the naphthalene, anthracene, naphthacene, naphtho (2,3-c) thiophene and benzo-c thiophene series are synthesized via the trapping of o-quinodimethanes by various dienophiles. Among these compounds, an intermediate for the synthesis of daunomycinone has been prepared and can be oxidized to a benzoquinone which provides access to new analogues of this important antileukemic agent. [Journal translation]

Tele-substitution reactions in the naphthalene series : The behaviour of 1,4 - dimethyl - 2 - nitro - 3 - phenylsulphonyl - and 2,3 - bisphenylsulphonyl - 1,4 - dimethyl - naphthalene towards sodium arenethiolates and secondary aliphatic amines

1,4 - Dimethyl - 2 - nitro - 3 - phenylsulphonylnaphthalene ( 2) reacts with sodium benzenethiolate in DMSO at 120° to give 1 - methyl - 2 - nitro - 4 - phenylthiomethylnaphthalene ( 4) [ tele-substitution product (TSP) of the phenylsulphonyl group] and 1,4 - dimethyl - 3 - phenylsulphonyl - 2 - phenylthionaphthalene ( 5) [normal substitution product (NSP) of the nitro group]. The analogous reactions of 2 with sodium 2,4,6- trimethylbenzenethiolate and of 2,3 - bisphenylsulphonyl -1,4 - dimethylnaphthalene ( 3) with sodium benzenethiolate or aliphatic amines give only TSPs of the phenylsulphonyl group. In the case of the reaction of 2 with aliphatic amines both the possible TSPs ( tele-substitution of the phenylsulphonyl or of the nitro group) were isolated in 9:1 relative yield. All the data show that the phenylsulphonyl is a leaving group far better than the nitro in such tele-substitution processes. The mechanism previously proposed to account for the formation of TSPs from 1,4-dimethyl - 2,3 - dinitronaphthalene is strongly supported by the obtained results.

An Efficient Steric Controlled Photo-Fries Rearrangement in the Naphthalene Series

An Efficient Steric Controlled Photo-Fries Rearrangement in the Naphthalene Series

Reactions of arylsulfonyl compounds with an excess of an organolithium reagent 13. Synthesis of o-mercapto sulfones and o-bissulfones of the benzene, naphthalene, and thiophene series from o-lithio sulfones

1. Methods have been developed for obtaining o-mercapto sulfones of the benzene, naphthalene, and thiophene series, and derivatives with transition-metal salts have been obtained for them. 2. The presence of an intramolecular hydrogen bond in the o-mercapto sulfones has been shown by IR spectroscopy, and spectral confirmation has been shown of the participation of the sulfonyl group in coordination with the metal in their metal derivatives. 3. A number of o-bissulfones and trissulfones of the benzene and thiophene series have been synthesized. The basic possibility of nucleophilic substitution of one of the sulfone groups in them has been shown.

Permselectivities of some aromatic compounds in organic medium through cellulose acetate membranes by reverse osmosis

Reverse osmosis of some aromatic compounds in 1-propanol solution using porous cellulose acetate membranes and some factors which influence the organic solute permeability were investigated. Reverse osmosis data for a number of benzene derivatives showed that only phenol was rejected and the others were enriched. For the compounds with various substituent groups, the solute permeabilities have the following order; OH < CH3 < H < Cl < NH2 < NO2. In the series of benzene, naphthalene, and anthracene, the permeability is related to the molar volume of solutes and varied as follows: benzene < naphthalene < anthracene. Generally speaking, there are two factors—a partition coefficient and a diffusion coefficient—for governing the permeation behavior through the membrane. Under the condition that no steric effect is exerted, the partition coefficient exclusively is a dominant factor. A good correlation between the partition coefficient of a particle and that of the membrane was pound. The partition coefficients are closely related to the dipole moment of solutes.

N.M.R. Spectral Studies of Some Quinolone Derivatives. Part VII.1Carbon-13 Magnetic Resonance Spectral Studies of N-Methyl-2-Quinolone Derivatives and an Examination ofperiSubstituent Effects

Abstract The 13C n.m.r. spectra of a series of 1-methyl-2-quinolone derivatives are presented. The N-CH3 and 8-CH3 carbons each exhibit a characteristic peri deshielding effect. The substituent effects caused by a peri-methyl group have been discussed and compared with effects previously observed in the naphthalene series.

13C chemical shifts in medium ring and macrocyclic ketolactones

Natural abundance 13C Ft nmr spectra of four different series of title compounds have been examined. Unambiguous chemical shift assignments could be made for all the carbons of the 11-membered cis-3,3-dimethyl-5-keto-6-alkyl-8-decenolides. In the rest of the 9- to 16-membered ketolactones, unique as well as logical assignments have been made using the standard 13C chemical shift rules. In the case of two benzo- and naphthoketolactone series examined, the available shielding parameters for the substituted benzenes were employed with success to the naphthalene series for the assignment of aromatic carbons.

Formula omitted] substitution in the naphthalene series. Reaction of 1,4-dimethyl-2,3-dinitronaphthalene with secondary aliphatic amines

1,4-Dimethyl-2,3-dinitro-naphthalin (I) reagiert mit den beiden sekundaren Aminen (II) zu den Substitutionsprodukten (III).

ChemInform Abstract: PHOTOSUBSTITUTION OF HALOGEN WITH A CYANO GROUP IN A NAPHTHALENE SERIES

Chemischer InformationsdienstVolume 7, Issue 13 Preparative Organic Chemistry ChemInform Abstract: PHOTOSUBSTITUTION OF HALOGEN WITH A CYANO GROUP IN A NAPHTHALENE SERIES A. N. FROLOV, A. N. FROLOVSearch for more papers by this authorA. V. EL'TSOV, A. V. EL'TSOVSearch for more papers by this authorO. V. KUL'BITSKAYA, O. V. KUL'BITSKAYASearch for more papers by this authorV. V. YUNNIKOV, V. V. YUNNIKOVSearch for more papers by this author A. N. FROLOV, A. N. FROLOVSearch for more papers by this authorA. V. EL'TSOV, A. V. EL'TSOVSearch for more papers by this authorO. V. KUL'BITSKAYA, O. V. KUL'BITSKAYASearch for more papers by this authorV. V. YUNNIKOV, V. V. YUNNIKOVSearch for more papers by this author First published: March 30, 1976 https://doi.org/10.1002/chin.197613118Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume7, Issue13March 30, 1976 RelatedInformation

Formula omitted] substitution in the naphthalene series. A kinetic study of the reaction of 2,3-dinitronaphthalene with piperidine in benzene

formula omitted] substitution in the naphthalene series. A kinetic study of the reaction of 2,3-dinitronaphthalene with piperidine in benzene

Synthesis and photolysis of some 1-naphthyl azoxy-compounds

Azoxy-compounds of the naphthalene series fail to undergo migration of the oxygen atom into the peri-position. This implies that the azo nitrogen function is intimately involved in the transfer process.

Platinum complexes with o-hydroxyazo compounds of the naphthalene series as efficient hydrogenation catalysts

Platinum complexes with o-hydroxyazo compounds of the naphthalene series as efficient hydrogenation catalysts

Directing effect of bases on the photo-reactions of polycyclic aromatic azides. Synthesis of “ [formula omitted]” azepines in the anthracene and naphthalene series.

Directing effect of bases on the photo-reactions of polycyclic aromatic azides. Synthesis of “ [formula omitted]” azepines in the anthracene and naphthalene series.

Arenonium ions' corresponding to the halogenation reactions of compounds of the naphthalene series

Arenonium ions' corresponding to the halogenation reactions of compounds of the naphthalene series

Investigation of 2,1,3-thia-and 2,1,3-selenadiazoles

The position of entry of the substituent in the electrophilic substitution of naphtho[1,2-d][2,1,3]thiadiazole depends on the nature of the attacking reagent: depending on the experimental conditions, 5-chloro and di,- and trichloro-substituted derivatives and 4-bromo and dibromo derivatives are formed during chlorination and bromination. In the absence of a catalyst, naphthothiadiazole is chlorinated by sulfuryl chloride to give 5-chloronaphthodiazole; 5-bromonaphthothiadiazole is formed with N-bromosuccinimide in the presence of anhydrous aluminum chloride. The 6-, 7-, 8-, and 9-amino derivatives of naphthothiadiazole are converted to the corresponding chloro and bromo derivatives by the Sandmeyer reaction. Depending on the experimental conditions, 4-sulfo (or chlorosulfo) and disulfo (or dichlorosulfo) derivatives are formed in the sulfonation and chlorosulfonation of naphthothiadiazole. As in the naphthalene series, the sulfo (or chlorosulfo) group can be replaced by chlorine (or bromine). Phthalic acid is obtained in the oxidation of 4-bromonaphthothiadiazole with potassium permanganate.

Reaction of acridine proton salts with arylamines in the presence of sulfur

The reaction of acridine proton salts with arylamines in the presence of sulfur was studied. It is shown that various arylamines of the benzene and naphthalene series, both free and substituted, form the corresponding aminoarylacridines in high yields in this reaction.

Kinetic and thermodynamic studies of acetals and ketals in the naphthalene series

Kinetic and thermodynamic studies of acetals and ketals in the naphthalene series

Solvation-induced line-width alternation in the electron spin resonance spectra of the meta-dinitrobenzene anion and of various symmetrically substituted dinitro-compounds in the benzene and naphthalene series

The e.s.r. spectra of a wide range of symmetrical radical anions of dinitrobenzene and dinitronapthalene in dimethyl-formamide–ethanol and ethanol–water are reported. Line-width alternation, which increased markedly with addition of ethanol to dimethylformamide solutions, is attributed to asymmetric solvation. Structural factors governing the rates of equilibration are discussed. N-Alkyl-2,6-dinitroaniline anions were abnormal in that asymmetry was relatively long lived even in dimethylformamide at room temperature. This is attributed to internal hydrogen-bonding between the anion proton and an oxygen atom of one nitro-group. Hydroxylamine has proved to be a useful reagent for the reduction of aromatic dinitro-compounds to their radical anions without spectral contamination by more highly reduced substances.

Properties of sodium bis(2-methoxyethoxy)aluminium hydride. XI. Reduction and hydrogenolysis of hydroxy-substituted aldehydes, ketones, carboxylic acids and carbinols of the naphthalene series

Properties of sodium bis(2-methoxyethoxy)aluminium hydride. XI. Reduction and hydrogenolysis of hydroxy-substituted aldehydes, ketones, carboxylic acids and carbinols of the naphthalene series

Rearrangement of hydrazo compounds

The rearrangement of hydrazo compounds in ionized and non-ionized acids has been investigated. The discussion of the mechanism in the presence of acids includes remarks on the rearrangement of 4,4′-disubstituted hydrazobenzenes. In the naphthalene series the thermal rearrangement of hydrazo compounds depends on the solvent used. The initial investigation included a study of the basicity of hydrazo compounds and the so-called dihydrohalides.