Diphenylmethane Derivatives Research Articles

Phenol oxidation mechanisms. A search for phenoxylium intermediates

Results which point to the occurrence of an ionic intramolecular coupling process in the oxidation of certain diphenyl ether and diphenylmethane derivatives are described. This process is in contrast to the usual free-radical coupling route encountered under different conditions. An attempt to induce a related heterolytic intramolecular coupling during the oxidation of some bis-hydroxynaphthylmethane monoethers was unsuccessful.

A new 2-phenyl-4H-1-benzopyran (flav-2-ene) synthesis

Phenoxymagnesium bromides react with cinnamaldehyde selectively in the position ortho to the oxy-substituent to yield diphenyl(styryl)methane derivatives (III). When a suitable substituent is located near the position of electrophilic attack, the reaction leads to mixtures of 2-phenyl-4H- and 2H-1-benzopyrans in a ratio which depends on the experimental conditions. The 2H-compounds are converted into the 4H-isomers when heated with alkoxy- or phenoxy-magnesium bromides. This method is the most straightforward route to 2-phenyl-4H-1-benzopyrans (flav-2-enes).

Hindered rotation in diphenylmethane derivatives. Part III. A comparison of NMR kinetic studies with the results of racemization measurements

AbstractThe NMR spectra of alkyl‐substituted diphenylmethane derivatives have been measured. In each compound investigated all chemically equivalent protons or group of protons were magnetically non‐equivalent due to hindered rotation. The activation parameters for the rotation of the phenyl groups in 2,4,2′,4′‐tetra‐tert. butyl‐6,6′‐dimethyldiphenylacetic acid were determined from variable temperature NMR experiments and were found to be in good agreement with the activation parameters for the racemization. Due to decomposition no kinetic measurements could be made on the benzhydrols and the benzhydryl methyl ethers.

Hydrogen and carbon scrambling in the molecular ions of diphenylmethane derivatives

Hydrogen and carbon scrambling precedes the losses of methyl radicals from m/e 168 and 167 in the spectra of diphenylmethane and its derivatives.

Formation of diphenylmethane derivatives during the Jacobsen reaction

Formation of diphenylmethane derivatives during the Jacobsen reaction

Macro Rings. I. Syntheses of a Novel Class of Compounds with a Chain of Alternating Benzene Rings and Methylene Groups

Abstract As starting materials for the synthesis of a macrocyclic compound, I, bridged diphenylmethane derivatives of the general formula p-XC6H4CH2(C6H4CH2)mC6H4X-p were synthesized; X is hydrogen or (CH2)nCOOR (n=0–3), m=2 or 3, and R=hydrogen or alkyl.

Cytochemical Studies with Acridine Orange and the Influence of Dye Contaminants in the Staining of Nucleic Acids

This chapter summarizes the salient information available about dye contaminants in four basic dyes comrnonly employed in the histochemical detection of nucleic acids. The fact that only four dyes, acridine orange (AO), basic fuchsin, methyl green, and the pyronins, are selected does not mean that there are no noteworthy contaminants in other dyes used in the staining of nucleic acids. This chapter focuses on cytochemical studies with acridine orange and the influence of dye contaminants in the staining of nucleic acids. Acridine orange is one of the more important diphenylmethane derivatives. The dye is prepared in a manner similar to that employed in the synthesis of pyronin Y (G). AO is one of a number of dyes which exhibits the phenomenon of metachromasy. This term refers to a property shared by many aniline dyes which undergo a major shift in their visible absorption bands to lower wavelengths following binding by many polyanions. In high concentrations of nucleic acids, a new absorption band appeared at longer wavelengths than the monomer band. Other basic dyes, like rosaniline, which do not polymerize in the free state, also interact with DNA to producc a spectral shift. With rosaniline it is observed that as the ionic strength of the dye solution decreases, there is an increase in the number of binding sites on DNA.

The synthesis of 1‐arylisochromans and their use in the preparation of ortho‐substituted diphenylmethane derivatives

AbstractSeveral 1‐arylisochromans were prepared from 1‐bromoisochroman and 1‐bromo‐4,4‐dimethylisochroman by reaction with arylmagnesium bromides. Bromination and heating yielded, presumably via bromo‐1‐arylisochromans, o‐(bromoalkyl)benzophenones. Treatment with lithium aluminium hydride converted the ketones into the corresponding carbinols, the side‐chain being simultaneously debrominated if sufficient hydride was used.Reactions of the bromoalkylbenzophenones with hydrazine derivatives yielded benzodiazepines.Treatment with hydriodic acid and red phosphorus converted 1‐phenyl‐isochroman into o‐(2‐iodoethyl)diphenylmethane while 4,4‐dimethyl‐1‐phenyl‐isochroman yielded 10,11‐dihydro‐10,10‐dimethyl‐5H‐dibenzo[a,d]cycloheptene and a compound (C13H10)n of unknown structure.

Effects of minor tranquillizers on brain phosphate levels in vivo

Investigation of the effects of certain diphenylmethane derivatives, chlordiazepoxide, meprobamate and 1-(2′-tetrahydrofuryl)-1-ethylamino-2-phenylethane (WIN 19583-4) upon levels of adenine nucleotides, phosphocreatine and inorganic phosphate in the rat brain in vivo indicates that behavioural depression is associated with a fall in adenosine triphosphate and a rise in adenosine diphosphate levels. The behavioural stimulants had the reverse effects. Changes in the adenine nucleotide levels appear to be correlated with effects upon behaviour.

Synthesis of polymers from diphenylmethane derivatives with the aid of the polyrecombination reaction

1. In the polyrecombination of diphenylmethane derivatives polymers and oligomers are formed. 2. Probable structures, which are in accordance with the elementary analysis and the infrared spectra, are proposed for the polymers obtained. 3. It is shown that the tendency for polymer formation is less for diphenylmethane derivatives containing electron-accepting substituents than for diphenylmethane itself. It is suggested that the cause of this difference lies in the electron density of the C-H bond of the methylene group of such a substituted diphenylmethane. 4. Four polymers and six pure compounds were prepared and characterized.

Prolongation of thiopental anaesthesia with hydroxyzine, SA 97, thiethylperazine, and thioridazine

Four series of crossover experiments were carried out with mongrel dogs to determine whether hydroxyzine and SA 97 (diphenylmethane derivatives) and thiethylperazine and thioridazine (phenothiazine derivatives) prolong sleep induced by thiopental. It was found that hydroxyzine caused prolongation of thiopental sleep, but this effect was not consistent whereas the other three drugs invariably delayed recovery from thiopental.

The synthesis and properties of crystalline polymers of the type of poly‐p‐xylenes and polyphenylene methyl derivatives

AbstractFor the purpose of obtaining polymeric hydrocarbons of enhanced thermostability, linear polymers of regular structure of the type (CH2ArCH2)n and (ArCH2)a with aromatic units in the chain were synthesized. Polymers of the first type were obtained by reaction of metallic sodium with the dichloromethyl derivatives of benzene, m,‐ and p‐xylenes, diphenylmethane, diphenyl and naphthalene in dioxane medium at 20–25°C. The m‐xylene derivative had a CH2Cl group in the m‐position and the others, dichlorides in the p‐ or p,p′‐positions. The polymers were precipitated from the solutions on forming and after removal of excess sodium with the aid of methanol and elimination of the low molecular impurities they appeared as colorless powders of the composition of hydrocarbons, at times containing chlorine. X‐ray analysis of the polymers revealed the presence of a crystalline structure the degree of which varied, depending upon the structure. The polymers differed greatly in solubility and melting points. Thus naphthalene and diphenyl derivatives, evidently being crosslinked three‐dimensional polymers, did not dissolve even in boilling α‐bromonaphthalene and decomposed above 300° and 550° without melting, while derivatives of other hydrocarbons dissolved in bromonaphthlene, melted, and probably were linear polymers of low molecular weight. The m‐xylene derivative was distinguished by low crystallinity, low melting point (130–135°C.) and easily dissolved in chloroform even in the cold. Diphenylmethane derivatives with a more clearly expressed crystallinity melted at 250–255°C. and began to dissolve in α‐bromonaphthaline only at 130°C. p‐Xylene derivatives, like poly‐p‐xylylene, were highly crystalline and melted at 350°, but began to dissolve in bromonaphthalene only at 235°. The molecular weight of the soluble polymers could be determined (according to Rast's method) only for the soluble m‐xylene derivative, which, depending upon the conditions of formation, varied from 1850 to 4000. Polymers of the second type were obtained by polycondensation of aromatic hydrocarbons with paraform and also with the dichloro‐, dioxy‐, and diacetoxymethyl derivatives of aromatic hydrocarbons in boiling glacial acetic acid containing sulfuric acid. In this way starting from p‐xylene and durene one could obtain high‐melting crystalline polymers with melting points above 250 and 320°, dissolving only in high boiling solvents. Condensation of durene with dichloromethyl derivatives of p‐ and m‐xylene as well as with p‐xylylene chloride led to the formation of high melting polymers of the type (ArCH2Ar′CH2)n containing two different aromatic units in the chain.

Use of intravenously given hydroxyzine for simple pain-producing office procedures.

There are many pain-producing procedures in dermatological practice for which it is impractical to use local blocking agents or general anesthesia. These occasions are unpleasant trials for the physician as well as the patient, especially when the latter is a child. Under such circumstances, an agent would be useful that could improve the patient's cooperation by allaying anxiety and apprehension and reducing hypermotility. It should, of course, be safe and preferably act quickly and for a short time without undesirable side-reactions. These criteria appear to be fulfilled by the use of intravenously given hydroxvzine hydrochloride (Vistaril). Chemistry and Pharmacology Hydroxyzine is classified as a piperazine and sometimes a diphenylmethane derivative. It has ataractic activity. In pharmacological doses it is nontoxic and well tolerated.' In mice, it decrease the motor activity and potentiates the anesthetic effect of hexobarbital. Intravenous injection in mice and rabbits induces a state of hypotony of limbs

Synthesis of polyarylenealkyls 9. Synthesis and transarylation of monofluoro- and monochlorodiphenylmethanes

1. m-and p-chloro derivatives and m-and p-fluoro derivatives of diphenylmethane were synthesized and it was shown that they undergo the transarylation reaction on being heated in the presence of aluminum chloride. m-Chloro-, m-fluoro-and p-fluorodiphenylmethanes were synthesized for the first time. 2. It was found that the halogen atoms located in para-position relative to the methylene group of diphenylmethane weaken the bond between the methylene group and the substituted atomatic nucleus; the halogen atoms located in meta-position relative to the methylene group do not exert any influence on the strength of this bond.

Relation of Structure of Diphenylmethane Derivatives to Toxicity to Tribolium confusum Duv.1

The toxicities to the confused flour beetle. Tribolium onfusum Duv., of 44 compounds related to diphenylmethane were compared. Two toxic mechanisms are suggested by time-mortality relationships as compared with dosage-mortality relationships. A DDT-type toxic mechanism appears to hold for the aliphatic substituted compound, while a more rapid diphenylmethane-type toxic mechanism is indicated for those with less aliphatic substitution. Replacement of benzene ling systems by other aromatic systems did not appreciably alter toxicity relationships.

ジフェニルメタンに対する細菌の耐性獲得について

ジフェニルメタンに対する細菌の耐性獲得について

ジフェニルメタンに対する細菌の耐性獲得について

ジフェニルメタンに対する細菌の耐性獲得について

Aromatic substitution meta to a basic group. Part II. Halogenation of diphenylmethane derivatives

The first page of this article is displayed as the abstract.

Heterocyclic Diphenylmethane Derivatives

Heterocyclic Diphenylmethane Derivatives

Antibacterial Activity of a Series of Diphenylmethanes

Thirty-eight derivatives of diphenylmethane were examined for antibacterial activity against a variety of organisms. Activity in vitro appeared more or less specific for Gram-positive bacteria, twenty-three derivatives being bactericidal for this type in concentrations ranging from 0.004 to 4.0mg. per cent, while only seven compounds were active against the respective Gram-negative organisms at levels of 0.5 to 4.0mg. per cent. Activity of the diphenylmethanes seemed to be dependent upon both hydroxy and halogen grou substitution in the parent structure, the position of these groups being of considrable importance. Substitution of various other groupings are discussed in an attempt to correlate chemical structure with activity. Antibacterial properties of the diphenylmethanes were markedly reduced in the presence of serum. Although the majority of compounds in the present series were found highly bactericidal for streptococci, none of the derivatives tested showed any marked protective action against experimental streptococcal infection in mice.