2132-70-9Relevant academic research and scientific papers
Oxidative dechlorination of methoxychlor by ligninolytic enzymes from white-rot fungi
Hirai, Hirofumi,Nakanishi, Sawako,Nishida, Tomoaki
, p. 641 - 645 (2004)
Ligninolytic enzymes, manganese peroxidase (MnP), laccase, and lignin peroxidase (LiP), from white-rot fungi were used in an attempt to treat methoxychlor (MC), a chemical widely used as a pesticide. MnP and laccase in the presence of Tween 80 and 1-hydroxybenzotriazole (HBT), respectively, and LiP were found to degrade MC, and MnP-Tween 80 decreased MC levels by about 65% after a 24-h treatment. MC was converted into methoxychlor olefin (MCO) and 4,4′-dimethoxybenzophenone by MnP-Tween 80 or laccase-HBT treatment. These results indicate that ligninolytic enzymes from white-rot fungi can catalyze the oxidative dechlorination of MC. Moreover, a metabolite MCO was also degraded by MnP-Tween 80 or laccase-HBT treatment.
Oxygenation by Superoxide Ion of CCl4, FCCl3, HCCl3, p,p'-DDT, and Related Trichloromethyl Substrates (RCCl3) in Aprotic Solvents
Roberts, Julian L.,Calderwood, Thomas S.,Sawyer, Donald T.
, p. 7691 - 7696 (1983)
In dimethylformamide (DMF) superoxide ion (O2-) oxygenates compounds with the trichloromethyl group: CCl4, HCCl3, and FCCl3 yield bicarbonate ion; PhCCl3 yields a mixture of PhC(O)OO- and PhC(O)O-; CF3CCl3 and HOCH2CCl3 give their carboxylate anions, RC(O)O-; and p,p'-DDT yields its dechlorinated product, DDE, which in turn reacts with O2- to give (p-ClPh)2C=O.Alkyl trichloromethyl compounds are unreactive within a 10-min reaction time at millimolar concentrations.The relative rates of reaction have been measured by the rotated ring-disc voltammetric method.On the basis of the relationship between the relative reaction rates and the electrophilic character of the substrates, as measured by the peak reduction potentials (Ep), the initial step is believed to be an electron transfer from the nucleophile to the electrophilic trichloromethyl group (a nucleophilic attack on chlorine with a concerted reductive displacement of Cl- and formation of RCCl2OO*).
Direct electrochemical reduction of 4,4-(2,2,2-trichloroethane-1,1-diyl)bis(methoxybenzene) (methoxychlor) at carbon and silver cathodes in dimethylformamide
McGuire, Caitlyn M.,Peters, Dennis G.
, p. G44 - G49 (2018/06/29)
Cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the electrochemical reduction of 4,4-(2,2,2-trichloroethane-1,1-diyl)bis(methoxybenzene), commonly known as the pesticide methoxychlor, at glassy carbon and silver cathodes in dimethylformamide (DMF) containing 0.050 M tetra-n-butylammonium tetrafluoroborate (TBABF4). Reduction of methoxychlor at both glassy carbon and silver shows four voltammetric peaks, the first three of which are associated with cleavage of carbon–chlorine bonds; the fourth peak is assigned to reduction of 4,4-(ethene-1,1-diyl)bis(methoxybenzene). Bulk electrolyses of methoxychlor at reticulated vitreous carbon and silver mesh cathodes at potentials corresponding to each of the first three voltammetric peaks were conducted; coulometric n values and product distributions (determined by means of GC and GC–MS techniques) depend on potential. In particular, two completely dechlorinated products, namely 4,4-(ethane-1,1-diyl)bis(methoxybenzene) and 4,4-(ethene-1,1-diyl)bis(methoxybenzene) have been identified and quantitated. A mechanistic scheme is proposed to account for the formation of the various products.
Kinetic and quantum chemical studies of the mechanism of dehydrochlorination of 2,2-diaryl-1,1,1-trichloroethanes with nitrite ions
Kazin,Kuzhin,Sirik,Guzov
, p. 1277 - 1281 (2016/10/26)
The E2 mechanism has been proposed for the dehydrochlorination of 2,2-diaryl-1,1,1-trichloroethanes with nitrite ion, leading to 2,2-diaryl-1,1-dichloroethenes, on the basis of experimental kinetic study and quantum chemical simulation.
Kinetic study of methoxide-promoted elimination reactions of some 1,1,1-trichloro-2,2-bis(phenyl-substituted)ethanes
Fontana, Gianfranco,Frenna, Vincenzo,Lamartina, Liliana,Natoli, Maria Concetta,Noto, Renato
, p. 108 - 114 (2007/10/03)
The methoxide-promoted elimination reaction of some 1,1,1-trichloro-2,2-bis(phenyl-substitute-d)ethanes (1) was investigated. The ortho-substituted derivatives were found to be less reactive than the corresponding ortho-unsubstituted derivatives, irrespec
Interaction of methoxychlor and related compounds with estrogen receptor α and β, and androgen receptor: Structure-activity studies
Gaido, Kevin W.,Maness, Susan C.,Mcdonnell, Donald P.,Dehal, Shangara S.,Kupfer, David,Safe, Stephen
, p. 852 - 858 (2007/10/03)
We previously demonstrated differential interactions of the methoxychlor metabolite 2,2-bis(p-hydroxyphenyl)-1,1,1-trichloroethane (HPTE) with estrogen receptor α (ERα), ERβ, and the androgen receptor (AR). In this study, we characterize the ERα, ERβ, and
Free radical elimination and oxidation of 1, 1, 1-trichloro-2, 2-bis(p-substituted phenyl)ethanes
Bennur, Shankar C.,Talawar, Mahadev B.,Laddi, Umesh V.,Nome, Faruk
, p. 74 - 76 (2007/10/03)
The reaction of 1, 1, 1-trichloro-2, 2-bis(p-substituted-phenyl)ethanes with bromine in carbon tetrachloride under nitrogen atmosphere and in the presence of light results in the formation of 1, 1-dichloro-2, 2-bis(p-substituted-phenyl)ethylenes. Whereas an identical reaction conducted under oxygen atmosphere, leads to the formation of benzophenone derivatives.
Darzens Reaction as a Convenient Method for the Synthesis of α-Chloroketones, α-Chloroepoxides, and Symmetrically Substituted Dioxines
Mamedov, V. A.,Litvinov, I. A.,Kataeva, O. N.,Rizvanov, I. Kh.,Nuretdinov, I. A.
, p. 1427 - 1436 (2007/10/02)
The Darzens reaction of dichloroacetophenone (DCAP) with substituted benzaldehydes has been studied.The structure of the products was shown to depend on the phenyl group substituents.Reaction of benzaldehyde, 4-bromo-, and 2,4-dichlorobenzaldehydes result
Synthesis of Substituted Fluorenones and Substituted 3',3'-Dichlorospiro and Their Reactivities
Chew, Warren,Hynes, Rosemary C.,Harpp, David N.
, p. 4398 - 4404 (2007/10/02)
Several novel 9-fluorenones were synthesized and were used as precursors in an attempt to prepare unique substituted 3',3'-dichlorospiro.Several of the thiiranes were unstable and desulfurized during their preparation (7a-d, 11, 12). 3',3'-Dichloro(2,5-dimethoxyspiro (7f) was prepared along with 2,2-dichloro-3,3-bis(4-methoxyphenyl)thiirane (16), and 3',3'-dichloro-10,11-dihydrospirocycloheptane-5,2'-thiirane> (17) all of which were stable at room temperature.A study of the reactivity of fluorenyl-substituted thiiranes and other related thiiranes showed that the extent of aromaticity of the substituents at the 3-position of the thiiranes influences their stabilities.
Reaction of α,β-Unsaturated Carboxylic Acids with Manganese(III) Acetate in the Presence of Chloride Ion
Yonemura, Hiroshi,Nishino, Hiroshi,Kurosawa, Kazu
, p. 3153 - 3160 (2007/10/02)
The reaction of 3-phenylpropenoic acids with manganese(III) acetate - Cl- complex yielded 1,2,2-trichloro-1-phenylethanes, 1-acetoxy-2,2-dichloro-1-phenylethanes, and 2,2-dichloro-1-phenylethanols. (E)-2,3-Diphenylpropenoic acids gave 2,2-dichloro-1,2-diphenylethanones and 2-acetoxy-1,2-diphenylethanones. 3,3-Diphenylpropenoic acids yielded 2,2-dichloro-1,1-diphenylethenes, 1-acetoxy-2,2-dichloro-1,1-diphenylethanes, 2,2-dichloro-1,1-diphenyl-1-ethanols, and 2-hydroxy-2,2-diphenylethanal.Fluorenylideneacetic acid gave 9-chloro-9-(dichloromethyl)fluorene, 9-acetoxy-9-(dichloromethyl)fluorene, and 9-fluorenone. 1-Cyclohexenecarboxylic acid yielded 1,2-dichlorocyclohexanecarboxylic acid and 1-acetoxy-2-chlorocyclohexanecarboxylic acid.The reaction can be explained in terms of a free-radical mechanism involving manganese(III) acetate - Cl- complexation, addition of Cl. radical, decarboxylation, and the oxidation of chloroethenes which are the reaction intermediates.
