The Synthesis of Parathion and Some Closely Related Compounds

Fletcher, John H.; Hamilton, J. C.; Hechenbleikner, Ingenuin; Hoegberg, Erick I.; Sertl, B. J.; Cassaday, J. T.

doi:10.1021/ja01162a028

Cited by 98 publications

(38 citation statements)

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“…Me,TeCI2 was prepared by the reaction of TeCI, and Me4Sn in toluene at 60°C under reflux for 4 h based on a procedure previously reported for the preparation of Ph2TeC12 (24). Sodium/ammonium salts of alkylene (25) and diphenyl (26) The ammonium salt of diphenyl dithiophosphate (0.348 g, 1.16 mmol) was added to a solution of dimethyltellurium dichloride (0.133 g, 0.58 mmol) in toluene (15 mL). The reaction solution was refluxed at 30°C with stining for 2 h. The product solution was filtered to remove NH4C1 and any unreacted materials and the solvent removed under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, spectroscopic, and structural studies of dimethyltellurium(IV) alkylene and diphenyl dithiophosphates. Crystal structures of and

Drake¹,

Khasrou²,

Mislankar³

et al. 1994

Can. J. Chem.

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and -CH2CEt2CH2-, have been synthesized in 80-90% yields by reaction of the corresponding sodium or ammonium salts of the appropriate dithiophosphoric acids with dimethyltellurium dichloride in toluene. Me,Te[S,P(OPh),], was also prepared in a similar fashion. The compounds have been characterised by elemental analyses -and 'H, l3C, 3 '~, and ' 2 5~e NMR, infrared and Raman spectroscopy. = 0.0295. The immediate environment about tellurium in both molecules is that of the saw-horse structure typical of tellurium(1V) compounds with the two methyl groups equatorial and one sulfur atom from each dithiophosphate group occupying the axial positions. The consideration of the second sulfur atom as part of the coordinating sphere is discussed in terms of a modification of Pauling's approach to partial bond orders. The 'H NMR spectra suggest that these dithiophosphates may be fluxional in solution andlor that there is rapid exchange of the sulfur atoms.

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Section: Methodsmentioning

confidence: 99%

Synthesis, spectroscopic, and structural studies of dimethyltellurium(IV) alkylene and diphenyl dithiophosphates. Crystal structures of and

Drake¹,

Khasrou²,

Mislankar³

et al. 1994

Can. J. Chem.

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“…Potassium O,O-dibenzylphosphorodithioate, KS2P(O-CHz-C6Hs)z, was prepared by the general procedure for phosphorodithioate esters of Fletcher, Hamilton, Hechenbleikner, Hoegberg, Sertl & Cassaday (1950). Benzyl alcohol was refluxed with phosphorus pentasulfide and the resulting precipitate was treated with alcoholic potassium hydroxide.…”

Section: Methodsmentioning

confidence: 99%

The crystal structure of potassium O,O-dibenzylphosphorodithioate KS₂P(O–CH₂–C₆H₅)₂

Hazel¹,

Collin²

1972

Acta Crystallogr Sect B

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“…2). Nitrophenols are used in the synthesis of compounds such as carbofuran (177), parathion (47), fluorodifen (76), nitrofen, and bifenox (203). Dinitrophenols have been used in the production of all categories of pesticides (ovicides, insecticides, herbicides, fungicides, etc.)…”

Section: Synthetic Nitroaromatic Compoundsmentioning

confidence: 99%

Nitroaromatic Compounds, from Synthesis to Biodegradation

Parales

2010

Microbiol Mol Biol Rev

744

470

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SUMMARY Nitroaromatic compounds are relatively rare in nature and have been introduced into the environment mainly by human activities. This important class of industrial chemicals is widely used in the synthesis of many diverse products, including dyes, polymers, pesticides, and explosives. Unfortunately, their extensive use has led to environmental contamination of soil and groundwater. The nitro group, which provides chemical and functional diversity in these molecules, also contributes to the recalcitrance of these compounds to biodegradation. The electron-withdrawing nature of the nitro group, in concert with the stability of the benzene ring, makes nitroaromatic compounds resistant to oxidative degradation. Recalcitrance is further compounded by their acute toxicity, mutagenicity, and easy reduction into carcinogenic aromatic amines. Nitroaromatic compounds are hazardous to human health and are registered on the U.S. Environmental Protection Agency's list of priority pollutants for environmental remediation. Although the majority of these compounds are synthetic in nature, microorganisms in contaminated environments have rapidly adapted to their presence by evolving new biodegradation pathways that take advantage of them as sources of carbon, nitrogen, and energy. This review provides an overview of the synthesis of both man-made and biogenic nitroaromatic compounds, the bacteria that have been identified to grow on and completely mineralize nitroaromatic compounds, and the pathways that are present in these strains. The possible evolutionary origins of the newly evolved pathways are also discussed.

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The Synthesis of Parathion and Some Closely Related Compounds

Abstract: In a previous note1 we have described a method for the preparation of the important insecticidal compound O,O-diethyl O-p-nitrophenyl thiophosphate which is now called "parathion." The method was based upon the synthesis used by Schrader2 who first prepared the compound and

Cited by 98 publications

References 0 publications

Synthesis, spectroscopic, and structural studies of dimethyltellurium(IV) alkylene and diphenyl dithiophosphates. Crystal structures of and

Synthesis, spectroscopic, and structural studies of dimethyltellurium(IV) alkylene and diphenyl dithiophosphates. Crystal structures of and

The crystal structure of potassium O,O-dibenzylphosphorodithioate KS₂P(O–CH₂–C₆H₅)₂

Nitroaromatic Compounds, from Synthesis to Biodegradation

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The Synthesis of Parathion and Some Closely Related Compounds

Abstract: In a previous note1 we have described a method for the preparation of the important insecticidal compound O,O-diethyl O-p-nitrophenyl thiophosphate which is now called "parathion." The method was based upon the synthesis used by Schrader2 who first prepared the compound and

Cited by 98 publications

References 0 publications

Synthesis, spectroscopic, and structural studies of dimethyltellurium(IV) alkylene and diphenyl dithiophosphates. Crystal structures of and

Synthesis, spectroscopic, and structural studies of dimethyltellurium(IV) alkylene and diphenyl dithiophosphates. Crystal structures of and

The crystal structure of potassium O,O-dibenzylphosphorodithioate KS2P(O–CH2–C6H5)2

Nitroaromatic Compounds, from Synthesis to Biodegradation

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About

The crystal structure of potassium O,O-dibenzylphosphorodithioate KS₂P(O–CH₂–C₆H₅)₂