cas 59-50-7, 4-Chloro-3-methylphenol | Articles data

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Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)
N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information

(2021/01/04)

para-Selective chlorination of cresols and m-xylenol using sulfuryl chloride in the presence of poly(alkylene sulfide)s
Chlorination of o-cresol, m-cresol, and m-xylenol using sulfuryl chloride in the presence of a range of poly(alkylene sulfide)s and a Lewis acid (aluminum or ferric chloride) has been studied. The sulfur containing catalysts used led to the production of para-chlorophenols in high yields and higher para/ortho ratios than for reactions in the absence of such poly(alkylene sulfide)s. The effectiveness of the polymers was found to be dependent on the length of the spacer groups between the sulfur atoms. For example, polymers with shorter spacers provided high yields of 4-chloro-o-cresol (ca. 97%), while polymers with at least one longer spacer provided high yields of both 4-chloro-m-cresol (up to 94.6%) and 4-chloro-m-xylenol (up to 97.6%).
Smith, Keith,Hegazy, Amany S.,El-Hiti, Gamal A.
p. 345 - 356
(2020/03/23)

Regioselective chlorination of phenols in the presence of tetrahydrothiopyran derivatives
Four six-membered cyclic sulfides, namely tetrahydrothiopyran, 3-methyltetrahydrothiopyran, 4-methyltetrahydrothiopyran and 4,4-dimethyltetrahyrdrothiopyran have been used as moderators in chlorination reactions of various phenols with sulfuryl chloride in the presence of aluminum or ferric chloride. On chlorination of phenol, ortho-cresol and meta-cresol the para/ortho chlorination ratios and yields of the para-chloro isomers are higher than when no cyclic sulfide is used for all of the cyclic sulfides, but chlorination of meta-xylenol is less consistent, with some cyclic sulfides producing higher p/o ratios and others producing lower ratios than reactions having no sulfide present.
Smith, Keith,Williams, Des,El-Hiti, Gamal A.
p. 529 - 538
(2019/06/13)

Ion-Pair-Directed Borylation of Aromatic Phosphonium Salts
Control of positional selectivity in C-H activation reactions remains a challenge for synthetic chemists. Noncovalent catalysis has the potential to be a powerful strategy to address this challenge. As a part of our ongoing investigations into the use of ion-pairing interactions in site-selective catalysis, we demonstrate that several classes of aromatic phosphonium salts undergo iridium-catalyzed C-H borylation with a high selectivity for the arene meta position. This is achieved using a bifunctional bipyridine ligand bearing a pendant sulfonate group, which had previously been successful for borylation of aromatic ammonium salts. In this case, the phosphonium salts give a higher meta selectivity than the corresponding ammonium salts. We propose that the high selectivity occurs due to an attractive electrostatic interaction between the substrate and the ligand in the transition state for borylation.
Lee, Bernadette,Mihai, Madalina T.,Stojalnikova, Violeta,Phipps, Robert J.
p. 13124 - 13134
(2019/06/17)

Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl
Chlorination of aromatic compounds underwent magnificent rate accelerations in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic hydrocarbons in the presence of KCl and KHSO4. Reaction times reduced highly significantly from 4-5 h in conventional protocol to 30-40 min under sonication, followed by high yields of monochloro derivatives as products with high regioselectivity.
Rajanna,Rao, A. Sambashiva,Chakravarthi,Reddy, K. Rajendar
p. 167 - 170
(2017/12/26)

Regioselective synthesis of important chlorophenols in the presence of methylthioalkanes with remote SMe, OMe or OH substituents
Various methylthio alcohols, methoxy(methylthio)alkanes and bis(methylthio)alkanes have been used as regioselectivity modifiers in the chlorination reactions of various phenols at room temperature. The process involves the use of a slight excess of sulfuryl chloride in the presence of aluminum or ferric chloride as an activator. Methylthio alcohols, methoxy(methylthio)alkanes and bis(methylthio)alkanes having 2 and 3 methylene groups as a spacer were found to be good for the para-selective chlorination of o-cresol and phenol. On the other hand, methylthio alcohols, methoxy(methylthio)alkanes and bis(methylthio)alkanes having 6 and 9 methylene groups were found to be good for the selective para-chlorination of m-xylenol and m-cresol. Calculations using density functional theory on bis(methylthio)alkanes have suggested two different types of stable chlorinated intermediates depending on the number of methylene units as a spacer.
Smith, Keith,Al-Zuhairi, Ali J.,Elliott, Mark. C.,El-Hiti, Gamal A.
p. 607 - 621
(2018/07/13)

Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants
Cytochrome P450 CYP102A1 (P450 Bm3) variants were used to investigate the products arising from the P450 catalysed oxidation of a range of disubstituted benzenes. The variants used all generated increased levels of metabolites compared to the wild-type enzyme. With ortho-halotoluenes up to six different metabolites could be identified whereas the oxidation of 2-methoxytoluene generated only two aromatic oxidation products. Addition of an ethyl group markedly shifted the selectivity for oxidation to the more reactive benzylic position. Epoxidation of an alkene was also preferred to aromatic oxidation in 2-methylstyrene. Significant minor products arising from the migration of one substituent to a different position on the benzene ring were formed during certain P450-catalysed substrate turnovers. For example, 2-bromo-6-methylphenol was formed from the turnover of 2-bromotoluene and the dearomatisation product 6-ethyl-6-methylcyclohex-2,4-dienone was generated from the oxidation of 2-ethyltoluene. The RLYF/A330P variant altered the product distribution enabling the generation of certain metabolites in higher quantities. Using this variant produced 4-methyl-2-ethylphenol from 3-ethyltoluene with ≥90 % selectivity and with a biocatalytic activity suitable for scale-up of the reaction.
Munday, Samuel D.,Dezvarei, Shaghayegh,Lau, Ian C.-K.,Bell, Stephen G.
p. 2512 - 2522
(2017/07/12)

Highly Selective Synthesis of Chlorophenols under Microwave Irradiation
Oxychlorination of various phenols is finished in 60 minutes with high efficiency and perfect selectivity under microwave irradiation. These reactions adopt copper(II) chloride (CuCl2) as the catalyst and hydrochloric acid as chlorine source instead of expensive and toxic ones. Oxychlorination of phenols substituted with electron donating groups (methyl, methoxyl, isopropyl, etc.) at ortho- and meta-positions is accomplished with higher conversion rates, lower reaction time, and excellent selectivity. A proposed reaction mechanism is deduced; one electron transfers from CuCl2 to phenol followed by the formation of tautomeric radical that can be rapidly captured by chlorine atom and converts into para-substituted product.
Xiong, Yawen,Duan, Hongdong,Meng, Xia,Ding, Zhaoyun,Feng, Weichun
(2016/06/14)

A process for synthesizing the between chlorine -cresol green
The invention provides a green synthesis technique of p-chloro-m-cresol, which comprises the following step: reacting by using m-cresol as a raw material, tetrachloroethylene as a solvent and sulfuric chloride as a chlorinating agent to prepare the p-chloro-m-cresol, wherein the mole ratio of the m-cresol to the tetrachloroethylene is 1:(0.5-1.5), and the mole ratio of the m-cresol to the sulfuric chloride is 1:(0.9-1.1).Compared with the prior art, the technique provided by the invention has the advantages of short reaction time, high solvent recovery rate, clean and environment-friendly production process and high degree of automation, and the m-cresol conversion rate after the reaction finishes is up to 98%; and thus, the technique has favorable industrialization prospects.
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Paragraph 0031-0033

(2017/06/24)

Comparison of cyclic and polymeric disulfides as catalysts for the regioselective chlorination of phenols
Two cyclic and two polymeric disulfides have been synthesized and established to be useful catalysts for the chlorination of m-xylenol, o-cresol, m-cresol and phenol using freshly distilled sulfuryl chloride in the presence of aluminum or ferric chloride as a co-catalyst at room temperature. The yields of p-isomers and para/ortho ratios were higher compared to cases where no catalyst was used with most catalysts for most phenols even when a very low concentration of disulfide was used.
Smith, Keith,Al-Zuhairi, Ali J.,El-Hiti, Gamal A.,Alshammari, Mohammed B.
p. 74 - 85
(2015/10/20)

Ferrocene tagged functional polymer: A robust solid-phase reagent for O-demethylation
Ferrocene tagged functional polymer was synthesized by exploiting the propensity of the Merrifield resin to undergo quaternization with N-ferrocenylmethyl benzimidazole followed by subsequent anion metathesis reaction. The synthesized polymer when employed as a solid-phase reagent for O-demethylation of aryl methyl ethers, showed TON in the range of 7373-8930 and TOF in the range of 279-494 h-1.
Kurane, Rajanikant,Gaikwad, Vipul,Jadhav, Jagannath,Salunkhe, Rajashri,Rashinkar, Gajanan
p. 6361 - 6366,6
(2012/12/12)

Bifunctional Aryloxylate Esters as potential oxidatively cleavable linkers
Selectively cleavable linkers are essential parts in environmentally responsive materials. Here, we introduce aryl oxalate esters (AOE) as one of the first examples for oxidatively cleavable linkers. To this end a series of novel AOEs was synthesized and explored regarding the H2O 2-dependent degradation. All AOEs were cleaved selectively at the oxalate group. The degradation rate was clearly dependent on the substituents. Further, it was found that the H2O2 based degradation undergoes an autocatalysis mechanism.
Czarnecki,Kampert,Barbe,Tiller
scheme or table
p. 3551 - 3554
(2011/07/29)

Novel highly selective catalytic oxychlorination of phenols
The highly selective oxychlorination of various phenols catalyzed by CuCl2 under mild conditions, in which chloride ions are used as chlorinating agents and dioxygen as a final oxidant, has been developed. The Royal Society of Chemistry 2006.
Menini, Luciano,Gusevskaya, Elena V.
p. 209 - 211
(2008/02/07)

Investigations of the reactions of monochloramine and dichloramine with selected phenols: Examination of humic acid models and water contaminants
The phenols are an important area of investigation because they are substituents in the humic acids and are common contaminants in water. The reactivities and orientations of two common phenols (phenol and m-cresol), and some of their chlorinated intermediates with aqueous monochloroamine and dichloroamine were presented. m-Cresol was more reactive than phenol with both chlorinating agents. NH2Cl and NHCl2 showed extensive reactivity toward the phenols, even the partially chlorinated less reactive intermediates would be expected to fully chlorinate the activated positions in phenolic substituents in the humic acids.
Heasley, Victor L.,Fisher, Audra M.,Herman, Erica E.,Jacobsen, Faith E.,Miller, Evan W.,Ramirez, Ashley M.,Royer, Nicole R.,Whisenand, Josh M.,Zoetewey, David L.,Shellhamer, Dale F.
p. 5022 - 5029
(2008/04/18)

A simple, efficient and regioselective oxychlorination of aromatic compounds using ammonium chloride and oxone
A simple, efficient, mild and regioselective method for oxychlorination of aromatic compounds is reported. The electrophilic substitution of chlorine generated in situ from NH4Cl as a chlorine source and oxone as an oxidant is reported for the first time.
Narender,Mohan, K.V.V. Krishna,Srinivasu,Kulkarni,Raghavan
p. 1335 - 1338
(2007/10/03)

Kinetics of chlorination of phenol and monosubstituted phenols by t-butyl hypochlorite in aqueous alkaline medium
The kinetics of chlorination of the parent and sixteen monosubstituted phenols (2-chloro, 2-methyl, 2-carboxy, 2-nitro, 3-chloro, 3-methyl, 3-carboxy, 4-fluoro, 4-chloro, 4-bromo, 4-methyl, 4-ethyl, 4-methoxy, 4-carboxy, 4-acetyl and 4-nitro) by t-BuOCl have been studied in aqueous alkaline medium. The rates of reactions show first order kinetics each in |t-BuOCl| and |XC 6H4OH| and inverse first order in |OH-|. Variation in either ionic strength or addition of reaction product has no significant effect on the rates of reactions, while lowering of the dielectric constant of the medium increases the rate. The rates are measured at different temperatures and the activation parameters for all the phenols computed. A mechanism involving the electrophilic attack of phenoxide ions by HOCl in the rate determining step is suggested. The rates decrease in the order: 3-CH 3 > 2-CH3 > 4-OCH3 > 4-CH3 > 4-C2H5 > H > 3-Cl > 3-COO- > 4-F > 2-COO- > 4-Br > 2-Cl > 4-Cl > 4-COO- > 4-COCH3 > 2-NO2 > 4-NO2. Hammett equation of the type, log k = -3.44 - 2.35 ρ is found to be valid for substituent effects. The enthalpy and entropy of activation are correlated.
Moodithaya,Gowda, B. Thimme
p. 420 - 425
(2007/10/03)

Process for the biocidal treatment of surface
Process for the biocidal treatment of surfaces, by applying an aqueous biocidal composition containing a biocidal agent (B), a surfactant (SA) when the said biocide is hydrophobic, and at least one water-soluble or water-dispersible organic copolymer (C) comprising at least one oligomeric or macromolecular unit (D) which can interact with the said biocide or with the micelles of surfactant(s) containing the said biocide when it is hydrophobic, and at least one hydrophilic macromolecular unit (E) which can interact with the surface to be treated and optionally with the said biocide. Use of the copolymer (C) in a biocidal composition for the treatment of surfaces, as an agent for the vectorization and/or controlled release of the said biocide onto the surface to be treated.
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(2008/06/13)

Influence of hydrogen bonding in the activation of nucleophiles: PhSH- (catalytic) KF in N-methyl-2-pyrrolidone as an efficient protocol for selective cleavage of alkyl/aryl esters and aryl alkyl ethers under nonhydrolytic and neutral conditions
The nucleophilicity of arenethiols can be augmented via hydrogen bonding with 'naked' halide anion. The activity of the halide anions follow the order F- ?Cl- ～ Br- ～ I- and is dependent on the countercation (Bu4N ～ Cs ～ K > Na ?Li). The solvent plays an important role in nucleophilic activation as well as regeneration of the effective nucleophile (e.g. ArS-) and those with high dielectric constant, high molecular polarizability, high donor number (DN), and low acceptor number (AN) are the most effective. Selective deprotection of alkyl/aryl esters and aryl alkyl ethers can be achieved under nonhydrolytic and neutral conditions by the treatment with thiophenol in 1-methyl-2-pyrrolidone (NMP) in the presence of a catalytic amount of KF. Aryl esters are selectively deprotected in the presence of alkyl esters and alkyl methyl ethers during intramolecular competitions.
Chakraborti, Asit K.,Sharma, Lalima,Nayak, Mrinal K.
p. 2541 - 2547
(2007/10/03)

Highly efficient, para-selective oxychlorination of aromatic compounds using potassium chloride and Oxone
A highly efficient, regioselective method for oxychlorination of aromatic compounds is possible through electrophilic substitution of chlorine generated in situ from KCl as a chlorine source and Oxone as an oxidant for the first time.
Narender,Srinivasu,Kulkarni,Raghavan
p. 279 - 286
(2007/10/03)

Kinetics and mechanism of chlorination of phenol and substituted phenols by sodium hypochlorite in aqueous alkaline medium
The kinetics of chlorination of the parent and thirteen substituted phenols (2-methyl, 2-chloro, 2-carboxy, 3-methyl, 3-chloro, 3-carboxy, 4-methyl, 4-ethyl, 4-chloro, 4-bromo, 4-carboxy, 4-acetyl and 4-nitro phenols) by NaOCl have been studied in aqueous alkaline medium under varying conditions. The rates show first order kinetics each in [NaOCl] and [(X)C6H4(OH)] and inverse first order in [OH-]. Variation in ionic strength of the medium and addition of Cl have no significant effect on the rates of reactions. The rates of the reactions are measured at different temperatures and the activation parameters for all the phenols computed. A mechanism involving the electrophilic attack of the phenoxide ions by NaOCl in the rate determining step has been considered. The values of the pre-equilibrium and the rate determining steps have been calculated for all the phenols. The rates decrease in the order: 3-CH3 >2-CH3 >4-C2H5 = 4-CH3 >phenol >3-COO = 3-Cl > 2-COO >4-COO >2-Cl ? 4-Cl ? 4-Br > 4-COCH3 >4-NO2. Hammett plot of the type, log kobs = -2.88 -3.2980σ is found to be valid. The correlation between the enthalpies and the free energies of activations is reasonably linear with an isokinetic temperature of 300 K. Further, the energies of activation of all the phenols are optimised corresponding to the log A of the parent phenol through the equation, Ea = 2.303 RT (log A - log kobs). Similarly log A values of all the phenols are optimised corresponding to the Ea of PhOH through the equation, log A = log kobs + Ea/2.303RT. Ea increases with the introduction of electron-withdrawing groups into the benzene ring, while the introduction of the electron-releasing groups lowers Ea for the reaction. Similarly log A decreases with the substitution of electron-withdrawing groups, while log A increases on substitution with the electron-releasing groups.
Gowda,Mary
p. 1196 - 1202
(2007/10/03)

A mild and chemoselective method for deprotection of aryl acetates and benzoates under non-hydrolytic condition
Chemoselective deprotection of aryl acetates and benzoates can be achieved under non-hydrolytic condition by treatment with K2CO3 in N-methyl-2-pyrrolidone (NMP) at 100°C. Selective cleavage of aryl acetates and benzoates take place in the presence of alkyl carboxylates during intramolecular competitions.
Chakraborti, Asit K,Sharma, Lalima,Sharma, Upasana
p. 9343 - 9346
(2007/10/03)

Selective deprotection of aryl acetates, benzoates, pivalates, and tosylates under nonhydrolytic and virtually neutral conditions
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Chakraborti, Asit K.,Nayak, Mrinal K.,Sharma, Lalima
p. 8027 - 8230
(2007/10/03)

Transition metal-catalyzed oxidations. 11 : Para-selective chlorination and bromination of phenols with tert-butyl hydroperoxide and TiX(OiPr)3
Mononuclear phenols 1-4 are chlorinated or brominated with high para-selectivity and in good yields to the halides 5-11 with the TiXn(OiPr)m/TBHP system (X = Cl or Br). WILEY-VCH Verlag GmbH, 1999.
Krohn, Karsten,Rieger, Hagen,Steingroever, Klaus,Vinke, Ingeborg
p. 59 - 61
(2007/10/03)

Agent for protecting sawn timber
The present invention relates to an agent or concentrate for protecting sawn timber against wood-discolouring fungi, containing a fungicide on phenol basis and a fungicide on organo-iodine basis, optionally fungicides and insecticides, dissolved in an organochemical solvent or solvent mixture or in a mixture of water and organochemical solvent or solvent mixture and at least one emulsifier.
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(2008/06/13)

Reactions of OH and SO4.- with Some Halobenzenes and Halotoluenes: A Radiation Chemical Study
The optical absorption and kinetic characteristics of the transients formed in the reactions of OH and SO4.- with bromobenzene, ortho and meta-isomers of chloro- and bromobenzenes, and monobromotoluenes have been studied by pulse radiolysis technique.The rates for OH reaction are generally higher (k = (1.7-4.4)X109 M-1s-1) than those found for the SO4.- reaction (k = (0.4-2.3)x109 M-1s-1). ρ+ values of -0.4 for OH and -1.2 for SO4.- reactions were obtained from the Hammett analysis.The formation of substituted hydroxycyclohexadienyl radicals (λmax = 315-330 nm) is the major reaction channel, and the phenoxyl type radical (λ >/=400 nm) formation is an additional minor process in the SO4.- reaction.Abstraction of H by SO4.- from the -CH3 group is only significant with the para-isomers of bromo- and chlorotoluenes.This result is in accord with the observed yields (70 percent of SO4.-) of the products resulting from the oxidation of the 4-chlorobenzyl radical in the presence of K3Fe(CN)6 under steady-state conditions.The total yields of the phenolic products accounting for >90 percent of OH and SO4.- suggest that the attack at the ipso positions is considerably small.The rate constants for OH reactions relative to benzene at positions 3 and 6 of 2-chlorotoluene and positions 2 and 3 of 4-chlorotoluene are between 1.18 and 1.39, indicating that the directing effects of -CH3 and -Cl groups are comparable.This is also reflected in the additive effects of activation of the ortho and para-positions and deactivation of meta-positions by these substituents in 3-chlorotoluene.
Merga, Getahun,Rao, B. S. M.,Mohan, H.,Mittal, J. P.
p. 9158 - 9164
(2007/10/02)

Photochemical Versus Aluminium Chloride-Catalyzed Fries Rearrangement of Aryl Hydrogen Succinates. Synthesis of 2(3H)-Furanones
The photochemical and aluminium chloride-catalyzed Fries rearrangement of a series of aryl hydrogen succinates 3 a-f to the corresponding 4-oxoacids 1 a-f are compared.Both approaches are complementary: the photochemical process is more general and becomes the method of choice for the succinoylation of phenols supporting alkoxy or hydroxy substituents, while the classical rearrangement is superior in the presence of alkyl or halogen substituents.These results are applied to the preparation of the 2(3H)-furanones 2 a-f. - Keywords: Fries rearrangement; Photo-Fries rearrangement; Aryl hydrogen succinates; 4-Oxoacids; 2(3H)-Furanones.
Fillol, Luis,Martinez-Utrilla, Roberto,Miranda, Miguel A.,Morera, Isabel M.
p. 863 - 870
(2007/10/02)

Method of disinfecting premises from coccidial oocysts using generated ammonia
A method of disinfecting premises from coccidial oocysts in which surface to be disinfected is thoroughly wetted with a first aqueous solution of ammonium salt containing approximately 0.5 to 1.5 molar of ammonium together with non-ionic surfactant and indicator having a color change in the region of pH 8 to pH 10 and the wetted surface is then covered with sufficient of a second aqueous solution of alkali metal hydroxide containing approximately 0.75 to 2.3 molar of hydroxide toether with phenolic bactericide to cause the indicator to change color on the treated surface. A preparation for use in such a method comprises a first package containing ammonium salt together with non-ionic surfactant and indicator and second package containing alkali metal hydroxide and phenolic bactericide, the molar amount of hydroxide in the second package being greater than the molar amount of ammonium in the first package.
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(2008/06/13)

Highly Selective Aromatic Chlorinations. Part 2. The Chlorination of Substituted Phenols, Anisoles, Anilines, and Related Compounds with N-Chloroamines in Acidic Solution
Phenols, anisoles, anilines, and related compounds are chlorinated in trifluoroacetic acid at room temperature by N-chlorodialkylamines and N-chlorotrialkylammonium salts.With monsubstituted compounds and their 2- and 3-substituted derivatives the reaction occurs efficiently and selectively at the 4-position.The reactivity of these substrates and the selectivity of their chlorinations are determined by electronic rather than steric effects of the substituent.Blocking the reaction with a substituent at the 4-position generally leads to only poor or moderate yields of the 2-chlorinated product.Evidence for radical and cation radical intermediates has been obtained in the reactions of some of the 4-substituted reactants and the mechanism of chlorination is discussed in the light of these findings.The reactions of selected substrates have been scaled up to give laboratory syntheses.
Smith, John R. Lindsay,McKeer, Linda C.,Taylor, Jonathan M.
p. 385 - 392
(2007/10/02)

Fungicidal 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles
Novel compounds of the class of 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles having fungicidal and plant-growth regulating properties.
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(2008/06/13)

Fluoran colorants for recording systems
Fluorans of the formula (I) STR1 where R1 is hydrogen or methyl, R2 is hydrogen or unsubstituted or substituted alkyl, R3 is hydrogen, unsubstituted or substituted alkyl, cycloalkyl or unsubstituted or substituted phenyl, or STR2 is a 5-membered or 6-membered saturated heterocyclic radical, R4 and R5 independently of one another are each hydrogen, alkyl, alkoxy or halogen, R6 is hydrogen, halogen, alkyl, alkoxy, phenylalkoxy, phenoxy, phenyl or unsubstituted or substituted amino, or is pyrrolidinyl, piperidinyl or morpholinyl, R7 is hydrogen, alkyl or halogen, R8 is C1 -C5 -alkyl, and the radicals R4 and R5 and/or R6 and R7 together may furthermore each be a --CH=CH--CH=CH-- bridge, and the fused-on benzo ring may be further substituted, are used for the preparation of pressure-sensitive and heat-sensitive recording materials.
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(2008/06/13)

STUDIES ON 1-ARYLOXYSILATRANES, II. - HYDROLYTIC STABILITY OF 1-ARYLOXYSILATRANES
The effect of substituents in the benzene ring on the rate constants of the hydrolysis of 1-aryloxysilatranes was investigated.A good correlation of log k vs. Σ? was obtained suggesting SN2-Si mechanism of the hydrolysis of all the compounds studied.The influence of the salt effect and reaction medium on the rate constant was also examined.The activation energies were determined for six compounds.
Lukasiak, J.,Jamrogiewicz, Z.
p. 167 - 172
(2007/10/02)

HIGH SITE-SELECTIVITY IN THE CHLORINATION OF ELECTRON-RICH AROMATIC COMPOUNDS BY N-CHLORAMMONIUM SALTS.
N-Chlorammonium salts are efficient and very site-selective monochlorinating agents for electron-rich aromatic compounds.
Smith, John R. Lindsay,McKeer, Linda C.
p. 3117 - 3120
(2007/10/02)

PhSeCl AS A CHLORINATING AGENT FOR ACTIVATED BENZENE DERIVATIVES
Regiospecific chlorination of some aromatic compounds using benzeneselenyl chloride are reported.
Ayorinde, Folahan O.
p. 2077 - 2078
(2007/10/02)

NON-CONVENTIONAL OXIDATIVE CHLORINATION OF m-CRESOL
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Eckstein, Zygmunt,Smereczynski, Krzysztof
p. 659 - 660
(2007/10/02)

Process for the arylation of olefines
A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide. The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.
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(2008/06/13)