cas 298-06-6, Diethylphosphorodithioate | Articles data

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Unusual behavior of 3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one towards some phosphorus reagents: Synthesis of novel diethyl 2-phosphonochromone, diethyl 3-phosphonopyrone and 1,3,2-oxathiaphosphinines
The chemical reactivity of 3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one (1) towards some phosphorus reagents was studied. The enaminone 1 was cyclized into diethyl 2-phosphonochromone 2 via its treatment with diethyl phosphite in basic medium. However, its reaction with triethoxy phosphonoacetate gave the substituted pyrone phosphonate 3. In addition, two novel examples of 4-(dimethylamino)-6-(2-hydroxyphenyl)-2-sulfido-4H-1,3,2-oxathia-phosphinines 6 and 7 were obtained from treatment of enaminone 1 with O,O-diethyl dithiophosphoric acid and Lawesson’s reagent. When enaminone 1 was also treated with phosphorus decasulfide, it was turned into 4H-thiochromene-4-thione while its treatment with phosphorus tribromide, phosphorus oxychloride, or phenylphosphonic dichloride, 4H-4-oxo-chromene was isolated in all cases. The possible reaction mechanisms of the formation of these products were discussed. The structures of newly isolated products were established by elemental analysis and spectral tools.
Ali, Tarik E.,Assiri, Mohammed A.,Yahia, Ibrahim S.,Zahran, Heba Y.
p. 550 - 557
(2019)
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A convenient route to novel fluorinated 1, 2, 4, 3-triazaphospholo[1, 5-a]pyridines and pyrido[1, 2-b][1, 2, 4, 5]triazaphosphinines
A simple synthetic approach to the construction of novel fluorinated 5-oxo(thioxo)-2-oxido(sulfido)-1, 2, 4, 3-triazaphospholo[1, 5-a]pyridines 2-14 and pyrido[1, 2-b][1, 2, 4, 5]triazaphosphinines 16, 19 and 22, was achieved. The method depends on the treatment of 1, 6-diamino-4-(4-fluorophenyl)-2-oxo-1, 2-dihydropyridine-3, 5-dicarbonitrile (1) with some different types of phosphorus reagents such as phosphorus acid, and their esters, phosphorus halides as well as phosphorus sulfides. Structures of all the synthesized products were established by elemental analysis and spectral tools.
Assiri, Mohammed A.,Abdel-Kariem, Somaia M.,Ali, Tarik E.,Yahia
p. 240 - 253
(2018)
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Synthesis and cytotoxicity evaluation of some novel chromone annulated phosphorus heterocycles
Novel chromono[2,3-e][1,2,4,3]triazaphosphepines 3?7, chromono[2,3-d][1,3,2]diazaphosphinine 8, chro-monyl α-hydrazinophosphonic acid 10, chromono[3,2-d][1,2]azaphosphole 11 and diethyl N-chromony-lphosphonoacetamide 12 were synthesized from treatment of 2-amino-3-[(2-phenylhydrazinylidene)methyl]chromone (2) with some phosphorus reagents such as phosphorus halides, phosphorus sulfides, and phosphonic acid and its diesters, in dry dioxane. The cytotoxic effects of the synthesized compounds were evaluated in vitro in relation to hepatocellular Hep-G2, breast MCF-7 and colon HCT-116 human cancer cell lines, using a crystal violet viability assay. Compounds 6, 7, 8, and 10 had significant cytotoxic effects against the three cancer cell lines. Their IC50 values ranged between 1.56 and 12.4?μg/mL in comparison to doxorubicin (IC50 = 0.426-0.469?μg/mL).
Ali, Tarik E.,Ibrahim, Magdy A.,El-Edfawy, Somaya M.
p. 819 - 826
(2017)
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Synthesis of novel 3-phenyl-2-oxido/sulfido-1,3,4,2-benzoxadiazaphosphepines
An efficient and facile synthetic approach towards a series of novel 3-phenyl-2-oxido/sulfido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepines 2–7 was described. The method depended on the cyclocondensation of equimolar ratios of salicylaldehyde phenylhydrazone (1) with different examples of phosphorus halides and phosphorus sulfides in toluene containing triethylamine as a catalyst. In the same manner, the fusion of salicylaldehyde phenylhydrazone (1) with triethyl phosphate in the presence of DBU afforded the 2-ethoxy-1,3,4,2-benzoxa-diazaphosphepine 8, while a fusion of compound 1 with diethyl phosphite and tris(2-chloroethyl)phosphite led to the formation of new examples of 1,2-benzoxaphospholes 9 and 10, respectively. Interestingly, the reaction of compound 1 with diethyl ethoxycarbonyl phosphonate in ethanol containing DBU as a catalyst furnished the chromeno[3,4-d][1,2,3]diazaphosphole derivative 12 as a regioselective product.
Ali, Tarik E.,Assiri, Mohammed A.,Yahia
p. 1828 - 1837
(2018)
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Synthesis and in vitro antimicrobial, antioxidant, and antiproliferative activities of some new pyrano[2,3-c]pyrazoles containing 1,2-azaphospholes, 1,3,2-diazaphosphinines and phosphonate moieties
New 1,2-azaphosphole, 1,3,2-diazaphosphinine, and phosphonate derivatives containing pyrano[2,3-c]pyrazole moiety were achieved. The synthetic pathways depended on the reaction of 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile with some phosphorus reagents such as diethyl phosphite, phosphorus sulfides, and phenyl phosphorus halides under different conditions. Compounds 6 and 7 recorded potent antibacterial and antifungal activities with lower toxicity, while compounds 4 and 6 displayed promising antioxidative properties. Further, compounds 4 and 9 exhibited potent cytotoxic effects against MCF-7, HepG-2, and HCT-116 cancer cells. The early apoptotic cell death was observed by the compounds in all types of the treated cells. Compounds 3, 5, 7, 10, and 14 recorded low to moderate percentages of necrosis and late apoptosis toward all treated cells.
Ali, Tarik E.,Assiri, Mohammed A.,El-Shaaer, Hafez M.,Abdel-Kariem, Somaia M.,Abdel-Monem, Wafaa R.,El-Edfawy, Somaya M.,Hassanin, Noha M.,Shati, Ali A.,Alfaifi, Mohammad Y.,Elbehairi, Serag Eldin I.
supporting information
p. 2478 - 2497
(2021/06/30)

Green synthesis technology of O,O-diethyl thiophosphoryl chloride
The invention provides a green synthesis technology of O,O-diethyl thiophosphoryl chloride and relates to the field of chemical synthesis. The green synthesis technology comprises the following steps:taking O,O-diethyl dithiophosphate to react with chlorine gas at low temperature, so as to obtain a crude product of the O,O-diethyl thiophosphoryl chloride; then transferring the crude product to react at high temperature; enabling the residual O,O-diethyl dithiophosphate to further completely react with the chlorine gas. Meanwhile, in a high-temperature reaction process, a polymeric compound isprevented from being generated when a compound catalyst is used and sulfur monochloride impurities are completely removed through reaction, so that a byproduct sulfur has a crystalline state and a product more easily separated and purified. Moreover, HCl and sulfur-containing odorous gas are pumped away through applying negative pressure and the tail gas is absorbed to prevent air pollution. In awhole reaction process, technological water does not need to be added, so that wastewater is not generated and the treatment cost of sulfur-containing and phosphorus-containing wastewater is reduced.The technology has the advantages of simplicity in operation, easiness for obtaining raw materials, moderate reaction conditions, small pollution and environment friendliness.
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Paragraph 0029; 0030; 0031; 0036; 0037; 0038; 0043; 0044

(2019/03/06)

Characterization of Dialkyldithiophosphates as Slow Hydrogen Sulfide Releasing Chemicals and Their Effect on the Growth of Maize
Hydrogen sulfide is a key gasotransmitter for plants and has been shown to greatly increase their growth and survival in the presence of environmental stressors. Current methods for slowly releasing hydrogen sulfide use chemicals, such as GYY-4137, but these result in the release of chemicals not found in the environment, and chemicals used may lack structures that can be readily tuned to affect the rate of release of hydrogen sulfide. In this article, we describe the synthesis and slow release of hydrogen sulfide from dialkyldithiophosphates, which are a new set of hydrogen sulfide releasing chemicals that can be used in agriculture. The rates of hydrolysis of dibutyldithiophosphate and GYY-4137 were measured in water at 85 °C and compared with each other to investigate their differences. GYY-4137 is widely used as a chemical that slowly releases H2S, but its rate of release was not previously quantified. The release of hydrogen sulfide in water at room temperature was measured for a series of dialkyldithiophosphates using a hydrogen sulfide electrode. It was shown that the structure of the dialkyldithiophosphate affected the amount of hydrogen sulfide released. The final degradation products of dibutyldithiophosphate were shown to be phosphoric acid and butanol, which are chemicals found in the environment. This result was notable because it demonstrated that dialkyldithiophosphates degrade to safe, natural chemicals that will not pollute the environment. To demonstrate that dialkyldithiophosphates have potential applications in agriculture, maize was grown for 4.5 weeks after exposure to 1-200 mg of dibutyldithiophosphate, and the weight of corn plants increased by up to 39% at low loadings of dibutyldithiophosphate.
Carter, Justin M.,Brown, Eric M.,Irish, Erin E.,Bowden, Ned B.
(2019/11/03)

Facile synthesis of novel 6-methyl-5-phenyl-2-sulfido-1,2,3,5-tetrahydro-4H[1,2] oxazolo[4′,5′:5,6]pyrano[2,3-d][1,3,2]diazaphosphinines
A number of 6-methyl-5-phenyl-2-sulfido-1,2,3,5-tetrahydro-4H[1,2]oxazolo[4′,5′: 5,6]pyrano[2,3-d][1,3,2]diazaphosphinines 4–11 were synthesized via an interaction of tetraphosphorus decasulfide and Lawesson’s reagent under different conditions with 6-amino-3-methyl-4-phenyl-4H-pyrano[3,2-d][1,2]oxazole-5-carbonitrile (3). The reaction mechanisms for these products were discussed. Structures of the newly synthesized products were established on the basis of elemental analysis and spectral data.
Ali, Tarik E.,Assiri, Mohamed A.,Abdel-Kariem, Somaia M.,Yahia, Ibrahim S.
p. 472 - 482
(2018/04/02)

Synthesis, spectral characterization and antibacterial activity of O, O’-dialkyl and alkylene dithiophosphatogold (III)dichloride; crystal structure of [S2POCMe2CMe2O]AuCl2
O, O’-Dialkyl and alkylene dithiophosphatogold (III)dichloride complexes of the type [(RO)2PS2]AuCl2 and [S2POGO]AuCl2, where R = Et, nPr, iPr, iBu, Ph, cyclohexyl and cyclopentyl, where G = CMe2CMe2-, have been synthesized in 80-90% yields by reaction of the corresponding acid or sodium salts of the appropriate dithiophosphoric acids in 1:1 ratio with gold (III) chloride in dry dichloromethane at room temperature. The compounds have been characterized by elemental analyses, IR and (1H, l3C, and 31P) NMR. The crystal structure of [S2POCMe2CMe2O]AuCl2, was determined. These new complexes have shown their growth inhibiting potential against various bacterial strains with moderate to good activity.
Elkhaldy, Adnan A. S.,Gaikwad, Dnyaneshwar,Staples, Richard J.,Janen, Afef,Boni, Yannic
p. 871 - 876
(2019/02/05)

Free-metal dicarboxylic acid derivatives and antiwear additives and lubricant compositions comprising the same
The present invention relates to heavy-metal-free dicarboxylic acid derivatives and to a wear-resistant and lubricant composition comprising the same. The lubricant composition comprising a dicarboxylic acid derivative compound according to the present invention has superior abrasion resistance performance to abrasion resistance performance of a conventional lubricant oil composition, and even when used at a lower content than the conventional lubricant oil composition, more excellent effects are exhibited, wherein heavy metals are not used to be environment-friendly, thereby being usefully used as engine oil, lubricating oil for a transmission, gear-oil, turbine oil, operation oil, refrigerator oil, compressor oil, vacuum pump oil, bearing oil, sliding surface oil, crude oil, metal cutting oil, plastic working oil, heat-treated oil, lubricating oil or processed oil additives.COPYRIGHT KIPO 2017
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Paragraph 0264; 0265

(2018/02/27)

Z-Selective ring opening of vinyl oxetanes with dialkyl dithiophosphate nucleophiles
Dialkyl dithiophosphates selectively ring open vinyl oxetanes in excellent yields under mild reaction conditions to form useful allylic thiophosphate products with high Z-selectivity. The Royal Society of Chemistry 2013.
Guo,Njardarson
supporting information
p. 10802 - 10804
(2013/11/06)

Dialkyl (alkylene) dithiophosphate adducts of anhydrous stannous chloride: Synthesis, characterization, and biological activities
Dialkyl (alkylene) dithiophosphate adducts of stannous chloride were synthesized by the reaction of anhydrous tin(II) chloride (SnCl2) and dialkyl (alkylene) dithiophosphoric acid in a 1:1 molar ratio, under anhydrous reaction conditions, below 5 °C in a closed vessel. The newly synthesized adducts were characterized by physicochemical and spectroscopic techniques [FT-IR, NMR (1H, 31P, and 119Sn), and mass spectrometry]. Coordination modalities have indicated a donor-acceptor interaction between sulfur and tin(II) moieties, where tin(II) acts as a Lewis acid. The adducts were found to have significant antibacterial activity against Escherichia coli and Pseudomonas aeruginosa, and antifungal activity against Aspergillus niger and Candida albicans. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Mohsin, Mohammed,Nagar, Meena,Choudhary, Alka
p. 1331 - 1338,8
(2020/08/31)

An efficient synthesis of O,O- di propyl (E)-2-[1-methyl 2-oxopropylidene]phosphorohydrazidothiolate (E) oxime and its analogues: A potential marine toxin
An efficient method for the synthesis of Ptychodiscus brevis toxin O,O- di n-propyl (E)-2-[1-methyl 2-oxopropylidene]phosphorohydrazidothiolate (E) oxime (TG-1) and its analogues has been developed using thermally stable and recyclable silica gel and Na2SO4 as a condensing agent and water scavenger, respectively. The compounds were evaluated against fish Rasbora daniconius by determining the LC50 and LC90 values. The results of biological evaluation showed that these compounds have high degree of toxicity. Copyright Taylor & Francis Group, LLC.
Gupta, Arvind K.,Dubey,Parashar,Kaushik
scheme or table
p. 1892 - 1910
(2009/08/07)

Nucleophilic reactions of phorate and terbufos with reduced sulfur species under anoxic conditions
The reactions of phorate and terbufos with bisulfide (HS-), polysulfide (Sn2-), thiosulfate (S2O 32-), and thiophenolate (PhS-) were examined in well-defined aqueous solution under anoxic conditions to investigate their role in the degradations of phorate and terbufos. Reactions were monitored at various concentrations of reduced sulfur species to obtain the second-order rate constants. The reactivity of the reduced sulfur species decreased in the order Sn2- > PhS- > HS- > S 2O32-. Hydrolysis products, formaldehyde and diethyl disulfide/di-tert-butyl disulfide, indicated that OH-/H 2O attacked the carbon atom between the two sulfur atoms, the so-called thioacetal carbon, which is very reactive due to the presence of the two neighboring sulfur atoms. The reaction of phorate and terbufos with PhS - was investigated to study the transformation products in the reactions with reduced sulfur species. The transformation products demonstrated that the observed increase in rate constants in the reaction with reduced sulfur species compared to hydrolysis could result from the nucleophilic attack of reduced sulfur species at the α-carbon of the ethoxy group and at the thioacetal carbon atom. The temperature dependence of measured second-order rate constants of the reaction of phorate and terbufos with HS- over 25-50°C was investigated to explore activation parameters, which are not significantly different for phorate and terbufos. All of the observations may imply similar pathways in the degradation of phorate and terbufos in the presence of reduced sulfur species. Slightly higher hydrolysis rates of terbufos and second-order reaction rate constants for the reactions with sulfur species of terbufos compared with those for phorate are observed, which could be attributed to the slightly different substituents.
Gan, Qiu,Jans, Urs
p. 3546 - 3554
(2008/02/09)

Reaction of thiometon and disulfoton with reduced sulfur species in simulated natural environment
The reactions of thiometon and its ethyl analogue, disulfoton, with reduced sulfur species [e.g., bisulfide (HS-), polysulfide (S n2-), thiophenolate (PhS-), and thiosulfate (S2O32-)] were examined in well-defined aqueous solutions under anoxic conditions. The role of reduced sulfur species was investigated in the abiotic degradation of thiometon and disulfoton. Experiments at 25°C demonstrated that HS-, Sn2-, PhS-, and S2O32- promoted the degradation of thiometon to a great extent while only Sn2- and PhS- showed a small accelerating effect in the degradation of disulfoton. Reactions were monitored at varying concentrations of reduced sulfur species to obtain the second-order rate constants. The reactivity of the reduced sulfur species decreased in the following order: Sn 2- > PhS- > HS- ≈ S2O 32-. Transformation products were confirmed by standards or characterized by gas chromatography mass spectrometry. The results illustrate that multiple pathways occur in the reactions with reduced sulfur species, among which the nucleophilic attack at the α-carbon of the alkoxy group was the predominant pathway. Activation parameters of the reaction of thiometon and disulfoton with HS- were also determined from the measured second-order rate constants over a temperature range. ΔH≠ values indicated that the reactivity of thiometon toward HS- was much greater than for disulfoton. Nucleophilic attack at the alkoxy group was more important for thiometon than disulfoton. When the measured second-order rate constants at 25°C are multiplied by [HS-] and ∑[S n2-] reported in saltmarsh porewaters, predicted half-lives show that reduced sulfur species present at environmentally relevant concentrations may present an important sink for thiometon in coastal marine environments.
Gan, Qui,Jans, Urs
p. 7753 - 7760
(2007/10/03)

(Salen)Ti(IV) complex catalyzed asymmetric ring-opening of epoxides using dithiophosphorus acid as the nucleophile
A series of chiral bis-Schiff bases were synthesized starting from (1R,2R)-(+)-diaminocyclohexane, (+)-cis-1,2,2-trimethyl-1,3-diaminocyclopentane, (R)-2,2′-diamino-1,1′-binaphthalene, and (1S,2S)-diphenyl-1,2-ethanediamine. The enantioselective ring-opening of meso epoxides with dithiophosphorus acids catalyzed by a (salen)Ti(IV) complex formed in situ upon the treatment of Ti(OPr-i)4 and the aforementioned chiral Schiff base was realized. The resulting products were obtained with low to good enantioselectivities (up to 73% ee). The (salen)Ti(IV) complex containing the backbone of 1,2-diaminocyclohexane exhibited the best enantioselectivity. The substituents in dithiophosphorus acids and those on the salen aromatic ring have a significant influence on the reaction. Moderate enantioselectivity were obtained for the (salen)Ti(IV) complex catalyzed ring-opening of racemic monosubstituted epoxides. High regioselectivity was observed for the alkyl substituted epoxides, whereas poor regioselectivity was obtained for the aryl substituted ones.
Zhou, Zhenghong,Li, Zhaoming,Quanyong, Wang,Liu, Bing,Li, Kangying,Zhao, Guofeng,Zhou, Qilin,Tang, Chuchi
p. 5802 - 5809
(2007/10/03)

DITHIOPHOSPHATO-PLATINUM-COMPLEXES FOR THE TREATMENT OF CANCERS
Complex of formulas: (I), (II) or (III): which are suitable for the treatment of tumors.
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Page/Page column 26-27; 32

(2008/06/13)

Reductive cleavage of the halogen-phosphorus and sulfur-phosphorus bonds with alkali metals
The reduction of thiophosphorus acid chlorides with alkali metals (Na, K) in liq. NH3/THF solution, potassium anthracenide, and potassium napththalenide was investigated. It was found that these types of phosphorus compounds easily undergo reduction to 〉P-S- anions. It was also demonstrated that 〉P-O- and 〉P-S- anions as well very efficiently undergo sulfurization with elementary sulfur in liquid ammonia to yield 〉P(O)S- and 〉P(S)S- anions, respectively.
Stankiewicz, Marek,Nycz, Jacek,Rachon, Janusz
p. 330 - 339
(2007/10/03)

Pathways for the hydrolysis of phorate: Product studies by 31P NMR and GC-MS
A new intramolecular mechanism is proposed for the hydrolysis of phorate. 31P NMR was used to study the formation of P-containing products of phorate hydrolysis in situ. When hydrolysis was followed by 31P NMR, a dominant P-containing product was found and was identified to be diethyl dithiophosphate using methylation and GC-MS. Combining the data from phorate hydrolysis at three different temperatures, thermodynamic parameters were calculated. The contributions of various possible pathways to phorate hydrolysis are discussed.
Hong, Feng,Pehkonen, Simo O.,Brooks, Elwood
p. 3013 - 3017
(2007/10/03)

Spectroscopic Investigations on the Acidity of O,O'-Dithiophosphoric Acid Esters in Nonpolar Aprotic Solvents
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Dimmig, Th.,Wittg-Koehler, S.,Radig, W.,Hartmann, J.,Petri, Th.
p. 245 - 249
(2007/10/02)

Reactivity of epichlorohydrin towards O,O'-dialkyldithiophosphoric acids
The selectivity of the reaction between O,O'-dialkyldithiophosphoric acids and epichlorohydrin is studied by two different methods.New phosphorus triesters are synthesized; they are potential lubricant additives. - Keywords: epichlorohydrin / O,O'-dialkyldithiophosphoric acid / lubricant additive / chlorohydrin
Robert, Didier,Curci, Michele,Mieloszynski, Jean-Luc,Paquer, Daniel
p. 1015 - 1018
(2007/10/02)

PRODUCTS OF THE ALKALINE HYDROLYSIS OF S-CHLOROMETHYL AND S-(N-ETHOXYCARBONYL-N-METHYLCARBAMOYLMETHYL) O,O-DIETHYLPHOPHORODITHIOATE
The alkaline hydrolysis of S-chloromethyl O,O-diethyl phosphorodithioate (chlormephos) and of S-(N-ethoxycarbonyl-N-methylcarbamoylmethyl) O,O-diethyl phosphorodithioate (mecarbam) may involve attack by hydroxide ion at phosphorus with phosphorus-sulfur cleavage, at the substituted S-methyl carbon atom with sulfur-carbon cleavage or, in the case of mecarbam, at the carbonyl carbon atom with carbonyl-nitrogen cleavage.Further reaction of the initially-formed O,O-diethyl hydrogen phosphorodithioate with chlormephos may lead to the formation of additional products.
Hudson, Harry R.,Lynch, Vincent P.,Pianka, Max,Soares, Vera M.
p. 277 - 281
(2007/10/02)

Phosphorous-31 Nuclear Magnetic Resonance Study of the Mechanism and Kinetics of the Hydrolysis of Zinc(II) O,O-Diethyl Dithiophosphate and Some Related Compounds
31P NMR spectroscopy has been used to investigate the mechanism and kinetics of hydrolysis of Zinc(II) O,O-diethyl dithiophosphate (1) (ZDTP) in 1,2-dimethoxyethane solution at 85 deg C with ten equivalents of water.All major intermediates and products have been identified and the individual reaction rates determined.ZDTP was found to be hydrolyzed (k=2.35 x 10-4 s-1) to phosphoric acid (7) via O,O-diethyl S-hydrogen dithiophosphate (3) (khyd=1.35 x 10-2 s-1) and thiophosphoric acid (6) (khyd=0.78 x 10-5 s-1).O-Ethyl O,O-dihydrogen and O,O-diethyl-O-hydrogen phosphorothioates (8), (9), and ethyl dihydrogen phosphate (10) were produced as by-products of the reaction.From a study of the order of appearance of the intermediates and products, a detailed mechanism for the hydrolysis of ZDTP has been proposed.O-Ethyl O,S-dihydrogen phosphorothioate (4) and dithiophosphoric acid (5) are found to be intermediates.
Burn, Alan J.,Dewan, Sharwan K.,Gosney, Ian,Tan, Paul S. G.
p. 753 - 758
(2007/10/02)

Photochemistry of Pesticides, 10. Photodegradation of O,O-Diethyl-S(3,4-dihydro-4-oxobenzotriazin-3-yl-methyl)phosphorodithioate (Azinphos-ethyl)
The photodegradation of Azinphos-ethyl (1) in chloroform and methanol solution has been studied. 3,4-Dihydro-3-methyl-4-oxobenzotriazine (3), 3,4-dihydro-4-oxo-benzotriazine (5), O,O-diethyl-O(3-methylbenzotriazine-4-yl)phosphate (8), N-methylanthranilic acid (11) (in methanol: methyl ester 12), and sulfur have been isolated and characterized as photoproducts.The decay mechanism is discussed. - Azinphos Ethyl, Photodegradation, 4-Oxobenzotriazines, O-Phosphates, N-Methyl-anthranilic Acid
Abdou, W. M.,Sidky, M. M.,Wamhoff, H.
p. 907 - 910
(2007/10/02)

SOME STRUCTURAL CHEMISTRY OF ORGANOLEAD(IV) COMPOUNDS CONTAINING LEAD-SULPHUR BONDS. THE CRYSTAL AND MOLECULAR STRUCTURES OF TRIPHENYLLEAD BENZENETHIOLATE, Ph3PbSPh, TRIPHENYLLEAD O,O'-DIETHYLDITHIOPHOSPHATE, Ph3PbS2P(OEt)2, AND DIPHENYLLEAD BIS(O,O'-DIBENZYLDITHIOPHOSPHATE), Ph2Pb
The crystal and molecular structures of three organolead compounds containing lead-sulphur bonds are described.Crystals of triphenyllead benzenethiolate (I, C24H20Pbs) are in the monoclinic space group P21/c, with a 7.657, b 16.427, c 16.239 Angstroem, β 93.781 deg, Z=4; crystals of triphenyllead O,O'-diethyldithiophosphate (II, C22H25O2PPbS2), and diphenyllead bis(O,O'-dibenzyldithiophosphate) (III, C40H38O4PbS4) are both in triclinic space group P, with a 9.579, b 10.602, c 12.710 Angstroem, α 101.623, β 99.554, γ 100.719 deg, Z=2, and a 11.760, b 12.532, c 16.263 Angstroem, α 80.14, β 111.46, γ 112.41 deg, Z=2, respectively.Structures were determined by the heavy atom method using 2820, 2752, and 3084 independent, non-zero reflections with I>3?(I) for compounds I, II and III, respectively, collected using an automated four-circle diffractometer using Mo-Kα radiation (λ 0.71069 Angstroem).The refinements converged at conventional R-values of 3.44percent, 7.40percent and 7.68percent for I, II, and III, respectively.Both Ph3PbSPh and Ph3PbS2(OEt)2 form lattices comprising non-interacting molecules with geometries at lead only slightly distorted from tetrahedral.The distortion in the dithiophosphate is somewhat greater than in the benzenethiolate, and is accompanied by a marginally longer lead-sulphur distance (2.554(6) Angstroem vs. 2.515(2) Angstroem).The lead in Ph2Pb2 are coordinated in a distorted octahedral fashion by two mutually trans phenyl groups (angle CPbC 165.0(9) deg) and two anisobidentate dithiophosphate ligands, each forming one short bond (2.723(6), 2.679(6) Angstroem) and one long bond (2.940(7), 2.957(6) Angstroem) to lead.In the crystal lattice, adjacent pairs of molecules are linked by long (3.69(2) Angstroem) lead-sulphur contacts to give an overall equatorial arrangement.
Begley, Michael G.,Gaffney, Christine,Harrison, Philip G.,Steel, Andrew
p. 281 - 294
(2007/10/02)

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS XLVIII Synthesis of Dithioesters from P,S-Containing Reagents and Carboxylic Acids and Their Derivatives
2,4-Bismethylthio-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IIa, is prepared from O,O-dimethyldithiophosphoric acid, Ia, and P4S10 at 160 deg C. 2,4-Bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IIc, and 2,4-bis(4-phenyl-thiolphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IId, are prepared at 160 deg C from P4S10 and diphenylether and diphenylsulfides, respectively.Carboxylic acids RCOOH (R=CH3, C2H5, n-C3H7, n-C4H9, C6H5CH2, C6H5) react with compound Ia at 130 deg C to give the corresponding methyl dithioesters.Carboxylic acids RCOOH (R=C6H5-CH2, C6H5) react with compound Ib at 200 deg C for 15 min to give the corresponding ethyl dithioesters, while low boiling acids (R=CH3, C2H5, n-C3H7) yielded mixtures of the corresponding ethyl dithioester and ethyl carboxylate.Carboxylic acid chlorides RCOCl (R=ClCH2, C2H5, t-C4H9, C6H5CH2, C6H5, p-NO2C6H4) react with compound IIa at 80 deg C to give the corresponding methyl dithioesters in good yields.S-Substituted thioesters react with IIc at 85 deg C to give the corresponding dithioesters in good yields.Dihydro-2(3H)-furanone, VI, and 5-methyl-2(3H)-furanone, VII, react with IIa at 80 deg C to give dihydro-2(3H)-thiophenethione, VIII and 2,2'-dithiobis(5-methyl thiophene), IX, respectively.Also XI reacts with IIa, IIc, and IId to give VIII in nearly quantitative yields.
Yousif, N. M.,Pedersen, U.,Yde, B.,Lawesson, S.-O.
p. 2663 - 2670
(2007/10/02)

Process for reacting alcohols and/or phenols with phosphorus pentasulfide
The invention relates to a process wherein an alcohol and/or phenol is reacted with phosphorus pentasulfide in the presence of a catalyst which is selected from (a) phosphonium salts of the general formula: STR1 (b) ammonium salts of the general formula: STR2 (c) phosphine oxides of the general formula: STR3 (d) phosphine sulfides of the general formula: STR4 (e) phosphinic acid derivatives of the general formula: STR5 In formulae I through V, the substituents R1, R2, R3 and R4 each stand for identical or different alkyl-, aryl-, alkaryl- or aralkyl- groups having from 1 to 22 carbon atoms. A stands for an inorganic or organic acid, and X and Y, respectively, stand for both oxygen and sulfur, and M stands for a monovalent metal or oxygen.
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(2008/06/13)

REDOX REACTIONS OF ANTIMONY(III) O,O-DISUBSTITUTED PHOSPHORODITHIOATES WITH FERRIC CHLORIDE
The reaction of antimony(III) tris-(O,O-diethylphosphorodithioate) with three equivalents of ferric chloride in ether solution has been found to give ferrous chloride, bis-(O,O-diethylthiophosphoryl) disulfide and dichloroantimony O,O-diethyl phosphorodithioate as the major products.However, a relatively low yield of bis-(O,O-diethylthiophosphoryl) trisulfide was also obtained.The structures of these products were established by independent syntheses.Several additional antimony(III) tris-(O,O-disubstituted phosphorodithioates) were prepared, and the major organic product obtained by reaction of each of these compounds with three equiva lents of ferric chloride was the corresponding bis-(O,O-disubstituted thiophosphoryl) disulfide.A mechanism for this reaction has been suggested, and evidence in support of the mechanism has been presented.The various antimony(III) tris-(O,O-dialkyl phosphorodithioates) are passivating agents in petroleum refining.The results reported in this and in our previous papers indicate that such compounds undergo a variety of reactions with components of crude petroleum prior to the ultimate pyrolysis reactions which occur in the fluid catalytic cracking process.
Woo, Edward J.,Kalbacher, Barbara J.,McEwen, William E.
p. 269 - 278
(2007/10/02)

REACTIONS OF ALIPHATIC ALCOHOLS WITH SULFUR AND RED PHOSPHORUS
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Mazitova, F. N.,Khairullin, V. K.
p. 1393 - 1396
(2007/10/02)

S-(α-substituted-arylmethylthio, -arylmethylsulfinyl, and -arylmethylsulfonyl)methyl phosphorus esters used as insecticides
There are provided novel S-(α-substituted -arylmethylthio, -arylmethylsulfinyl, and -arylmethylsulfonyl) methyl phosphorus esters of reduced mammalian toxicity and methods for controlling insects and acarids therewith. There are also provided methods for protecting plants from attack by insects and acarids by applying an insecticidally or acaricidally effective amount of the aforementioned esters to the foliage of said plants or to the soil in which they are grown.
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(2008/06/13)