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1.
Carlo Anchisi Luciano Corda Antonio Maccioni Gianni Podda Salvatore Cabiddu 《Journal of heterocyclic chemistry》1976,13(5):1033-1036
The preparation of 1,3,2-benzoxathia- and 1,3,2-benzodioxachlorostiboles (IIa-b) by reaction of antimony trichloride with 2-hydroxythiophenol (Ia) or 1,2-benzodiol (Ib) is described. The halogen was easily removed. Thus a Wurtz-like reaction gave the distibole compounds (IVa-b), which were also produced by organolithium compounds or pyridine. The compounds Va-b were obtained with sodium hydroxide, ethoxide and phenoxide, but spiran derivatives VIIa-b, of antimony, were obtained by treating IIa-b with 2-hydroxythiophenol or 1,2-benzodiol in the presence of triethylamine. The structure of the prepared compounds was determined by spectro-scopic methods. 相似文献
2.
Reena Agrawal Jyoti Sharma Durgesh Nandani Amala Batra Yashpal Singh 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3):471-480
Abstract Chloro-bis(2,2-dithio-1,3,2-dioxaphospholane/dioxaphosphorinane)bismuth(III) compounds have been synthesized by the reaction of bismuth trichloride with sodium 2,2-dithio-1,3,2-dioxaphospholane/dioxaphosphorinane in 1:2 molar ratio in benzene solution. Reactions of these chloro-bis(2,2-dithio-1,3,2-dioxaphospholane/dioxaphosphorinane)-bismuth(III) compounds with sodium tetraisopropoxyborate in equimolar ratio in benzene solution yield the corresponding heterobinuclear bismuth derivatives with boron. All compounds were characterized by elemental analyses and molecular weight measurements. Plausible structures are proposed on the basis of IR and 1H, 11B, 13C, and 31P spectroscopic studies. 2-Mercapto-2-thioxo-1,3,2-dioxaphospholanes-/dioxaphosphorinanes and the corresponding chloro-bis(2,2-dithio-1,3,2-dioxaphospholane/dioxaphosphorinane)bismuth (III) compounds show antifungal activities against Fusarium and Trichoderma. 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. GRAPHICAL ABSTRACT 相似文献
3.
A. E. Shipov G. K. Genkina O. I. Artyushin Z. O. Mndzhoyan B. E. Gushchin E. I. Chumakova S. A. Roslavtseva O. Yu. Eremina E. I. Bakanova Yu. S. Kagan E. A. Ershova T. A. Mastryukova M. I. Kabachnik 《Russian Chemical Bulletin》1995,44(11):2147-2156
Methods for the synthesis of 2-aryloxy(arylthio)- and 2-alkoxy(alkylthio)-2-thio(oxo)-1,3,2-oxazaphosphorinanes and theirN-substituted derivatives based on the reactions of the corresponding dichlorophosphates, dichlorothio-, and dithiophosphates with 3-aminopropan-1-ol or its substituted derivatives in the presence of Et3N or aqueous alkali under phase transfer catalysis conditions, as well as by the reaction of the tetramethylammonium salt of 2-hydroxy-2-thio-1,3,2-oxazaphosphorinane with alkyl- and acyl halides, by that of 2-chloro-2-thio-1,3,2-oxazaphosphorinane with sodium thiolates, and by other methods, were developed. The compounds obtained exhibit high nematocide activity but low toxicity for mammals. Some active synergists for permethrine were found among these compounds.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2241–2249, November, 1995.This study was financially supported in part by the International Science Foundation (Grant Nos. NDO 000 and NDO 300) and by the Russian Foundation for Basic Research (Grant No. 93-03-0451). The authors are grateful for this support. 相似文献
4.
Türsen Demir Frederick J. Raveney Robert A. Shaw 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3-4):155-163
Abstract The reactions of 4-methyl-2-[N-(p-toluidinyl)methyl]aniline with phosphorus oxychloride, thiophosphoryl chloride, and their derivatives yield 1,3,2-benzodiazaphosphorine 2-oxides and 2-sulphides. Their 1H NMR and infrared spectra are discussed. Related 1,3,2-benzodiazophosphorine and 1,3,2-dibenzodiazaphosphocine 2-oxides and 2-sulphides are compared. 相似文献
5.
On 1,3,2-Benzoxythioborols 2-Mercapto-4-methoxyphenol reacts with BCl3 giving the 2-Chloro-5-methoxy-1,3,2-benzoxythioborol. This compound reacts with phenol, thiophenol, 2-mercapto-4-methoxyphenol, sec. amines, lithium butyl and lithium phenyl and the corresponding 2-substituted products are obtained. With sodium two borol rings are connected resulting a boron-boron bond. The Lewis-acid behaviour of some of this compounds is investigated. 相似文献
6.
Carlo Anchisi Luciana Corda Anna Fadda Antonio Maccioni Gianni Podda 《Journal of heterocyclic chemistry》1982,19(3):649-652
The cleavage reaction of some 1,3,2-benzoxathiastannole, -arsole and -stibole derivatives with acetyl and benzoyl chloride is described. The reactions were carried out refluxing in benzene or at room temperature. In all cases, the reaction occurs through the initial cleavage of the S-M linkage with formation of the respective o-acylthio derivatives. The structure of the prepared compounds was assigned on the basis of their analytical, physical and spectral data. 相似文献
7.
Gary M. Coppola 《Journal of heterocyclic chemistry》1979,16(5):897-901
Novel fused tricyclic phosphorus heterocycles 9 and 11 and the tetracycle 15 were synthesized by cyclization of 1-haloalkyl (or 3-haloalkyl)-2,3-dihydro-1,3,2-benzodiazaphosphorin-4(1H)one 2-oxides with sodium hydride. Some spectral data of the products are also discussed. 相似文献
8.
Syntheses, Structures, Electrochemistry and Optical Properties of Alkyne‐Functionalized 1,3,2‐Diazaboroles and 1,3,2‐Diazaborolidenes The reaction of 2‐bromo‐1,3‐ditert‐butyl‐2,3‐dihydro‐1H‐1,3,2‐diazaborole ( 3 ) with lithiated tert‐butyl‐acetylene and lithiated phenylacetylene affords the 2‐alkynyl‐functionalized 1,3,2‐diazaboroles 4 and 5 as a thermolabile colorless oil ( 4 ) or a solid ( 5 ). Similarly 2‐bromo‐1,3‐diethyl‐2,3‐dihydro‐1H‐1,3,2‐benzodiazaborole ( 6 ) was converted into the crystalline 2‐alkynyl‐benzo‐1,3,2‐diazaboroles 7 and 8 by treatment with LiC≡C–tBu or LiC≡CPh, respectively. 2‐Ethynyl‐1,3‐ditert‐butyl‐2,3‐dihydro‐1H‐1,3,2‐diazaborole ( 2 ) was metalated with tert‐butyl‐lithium and subsequently coupled with 2‐bromo‐1,3,‐ditert‐butyl‐2,3‐dihydro‐1H‐1,3,2‐diazaborole ( 3 ) to afford bis(1,3‐ditert‐butyl‐2,3‐dihydro‐1H‐1,3,2‐diazaborol‐2‐yl)acetylene ( 9 ) as thermolabile colorless crystals. Analogously coupling of the lithiated species with 6 or with 2‐bromo‐1,3‐ditert‐butyl‐1,3,2‐diazaborolidine ( 11 ) gave the unsymmetrically substituted acetylenes 10 or 12 , respectively, as colorless solids. Compounds 4 , 5 , 7 – 10 and 12 are characterized by elemental analyses and spectroscopy (IR, 1H‐, 11B{1H}, 13C{1H}‐NMR, MS). The molecular structures of 5 , 8 and 9 were elucidated by X‐ray diffraction analyses. 相似文献
9.
The mass spectra of a series of 2-p-substituted phenyl-1,3,2-dioxaborolanes have been examined and compared with the mass spectrum of 2-phenyl-1,3,2-dioxaborolane. Formation of the substituted ion [C7H6X]+ by electron impact induced rearrangement has been found to be influenced significantly by the presence and nature of the substituent at the para position of the phenyl ring. 相似文献
10.
2-Phenoxy- and 2-dialkylamino-2-oxa-1,3,2-oxathiaphospholanes react with PCl5 with ring opening and formation of the corresponding acid chlorides of thiophosphoric acid. Under analogous conditions, 2-phenoxy-2-oxo-1,3,2-oxathiaphosphorinanes do not react with PCl5, while acid chlorides of thiophosphoric acid are formed in low yield along with other products in the reaction of 2-dialkylamino-2-oxo-1,3,2-oxthiaphosphorinanes with PCl5.A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Science Center, Russian Academy of Sciences, 420083 Kazan. Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 2676–2678, November, 1992. 相似文献
11.
Terent'eva S. A. Nikolaeva I. L. Burilov A. R. Kharitonov D. I. Popova E. V. Pudovik M. A. Litvinov I. A. Gubaidullin A. T. Konovalov A. I. 《Russian Journal of General Chemistry》2001,71(3):389-395
By reaction of calix[4]resorcinarene with 2-ethyl-1,3,2-benzoxazaphospholine in 1:1 ratio we prepared a cavitand possessing one dioxaphosphocinic fragment on the upper circle of the molecule. Reaction of the same compounds in ether solution in 1:4 and 1:8 ratio according to the data of spectral methods leads initially to formation of addition product, the P-H phosphorane with composition 1:4. This compound is not stable and on keeping forms 2-oxo-2-ethyl-1,3,2-benzoxazaphospholine, spirophosphorane, o-aminophenol and phosphorylated calixarene. In the reaction of the aminoalkylated calixarene with 2-ethyl-1,3,2-benzoxazaphospholine we isolated a compound possessing four hydrophoshonyl fragments on the upper circle of the calixarene matrix. 相似文献
12.
Synthesis and Reactivity of 2‐Bromo‐1,3‐diethyl‐2,3‐dihydro‐1 H ‐1,3,2‐benzodiazaborole Molecular Structure of Bis(1,3‐diethyl‐2,3‐dihydro‐1 H ‐1,3,2‐benzodiazaborol‐2‐yl The reaction of a slurry of calcium hydride in toluene with N,N′‐diethyl‐o‐phenylenediamine ( 1 ) and boron tribromide affords 2‐bromo‐1,3‐diethyl‐2,3‐dihydro‐1 H‐1,3,2‐benzodiazaborol ( 2 ) as a colorless oil. Compound 2 is converted into 2‐cyano‐1,3‐diethyl‐2,3‐dihydro‐1 H‐1,3,2‐benzodiazaborole ( 3 ) by treatment with silver cyanide in acetonitrile. Reaction of 2 with an equimolar amount of methyllithium affords 1,3‐diethyl‐2‐methyl‐2,3‐dihydro‐1 H‐1,3,2‐benzodiazaborole ( 4 ). 1,3,2‐Benzodiazaborole is smoothly reduced by a potassium‐sodium alloy to yield bis(1,3‐diethyl‐2,3‐dihydro‐1 H‐1,3,2‐benzodiazaborol‐2‐yl] ( 7 ), which crystallizes from n‐pentane as colorless needles. Compound 7 is also obtained from the reaction of 2 and LiSnMe3 instead of the expected 2‐trimethylstannyl‐1,3,2‐benzodiazaborole. N,N′‐Bis(1,3‐diethyl‐2,3‐dihydro‐1 H‐1,3,2‐benzodiazaborol‐2‐ yl)‐1,2‐diamino‐ethane ( 6 ) results from the reaction of 2 with Li(en)C≡CH as the only boron containing product. Compounds 2 – 4 , 6 and 7 are characterized by means of elemental analyses and spectroscopy (IR, 1H‐, 11B{1H}‐, 13C{1H}‐NMR, MS). The molecular structure of 7 was elucidated by X‐ray diffraction analysis. 相似文献
13.
Oxidative Derivatization of 1,3,2-Dioxaphosphorinanes Using Carbon Tetrachloride as Oxidant 2-Alkoxy- and 2-dialkylamido-1,3,2-dioxaphosphorinanes react with CCl4 in presence or absence of protic nucleophiles under ring opening forming acyclic derivatives of phosphates. 2-Anilido-1,3,2-dioxaphosphorinane, however, forms 2-amido-2-phenylimido-1,3,2-dioxaphosphorinanes ( 6 ) retaining the heterocyclic ring system. The latter are also obtained in the reaction of 2-dialkylamido-1,3,2-dioxaphosphorinanes with CCl4 and aniline. 2-Amino-2-oxo-1,3,2-dioxaphosphorinanes ( 8 ) are prepared from 2-hydrido-2-oxo-1,3,2-dioxaphosphorinane ( 7 ) by means of the Atherton-Todd reaction. In combination with the Staudinger reaction the latter yields N(2-oxo-1,3,2-dioxaphosphorinanyl)phosphazenes ( 10 ). 相似文献
14.
Koroteev A. M. Krasnov G. B. Koroteev M. P. Nifantyev E. E. 《Russian Journal of Organic Chemistry》2003,39(4):601-608
A series of 2-N and 2-O-substituted 2-oxo-4-chloromethyl-1,3,2-dioxaphosphorinanes were prepared by reaction of amines and alcohols with 2-oxo-2-chloro-4-chloromethyl-1,3,2-dioxaphosphorinane. The structure of compounds obtained was proved by means of 1H and 1
3C NMR spectroscopy. Some cyclic amidocyclophosphates possessed biological activity as inhibitors of mitotic fission and of Na+/H+ exchange. 相似文献
15.
Vasily A. Pinchuk Christian Müller Holger Thnnessen Peter G. Jones Reinhard Schmutzler Yuri G. Shermolovich 《无机化学与普通化学杂志》1996,622(7):1250-1256
The reactions of N,N′-dimethyl-N,N′-bis(trimethylsilyl)urea 8 and N-methyl-N′-phenyl-N,N′-bis(trimethylsilyl)urea 9 with phenylselenenyl chloride 6 and p-chlorophenylselenenyl chloride 7 furnished the N-arylseleno-N,N′-diorgano-N′-(trimethylsilyl)ureas 10–13 . The reactions of 10–13 with MePCl2 and PhPCl2 resulted in the formation of a new class of compounds, the 2-arylseleno-2-chloro-1,2,3-triorgano-1,3,2λ5-diazaphosphetidin-4-ones 14–19 . The new selenophosphoranes 20 and 21 were obtained in the reaction of 15 and 17 with p-nitrophenol in the presence of triethylamine. The identity and structure of the new compounds were established by 1H- and 13C-NMR spectroscopy, elemental analysis, 31P- and 77Se-NMR spectroscopy in the case of the selenophosphoranes 14–21 , and mass spectrometry in the case of 11 and 13 . A possible mechanism of the reaction leading to the selenophosphoranes is discussed. Single-crystal X-ray structure analyses of the selenophosphoranes 19 and 20 were conducted. Both display distorted trigonal bipyramidal geometry at phosphorus, the major distortions being imposed by the four-membered rings. 相似文献
16.
Dwight W. Chasar 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3-4):149-154
Abstract The reaction of 2,6-di-t-butyl-4-methylphenylphosphorodichloridite with α-diketones in the presence of magnesium metal affords modest yields of 1,3,2-dioxaphospholenes. This may be the first evidence for the existence of the monocoordinate aryloxyphosphinidene intermediate, ROP. 相似文献
17.
A. E. Shipov O. I. Artyushin G. K. Genkina A. V. Khrunin O. Yu. Eremina E. I. Bakanova S. A. Roslavtseva T. A. Mastryukova 《Russian Chemical Bulletin》2000,49(9):1593-1597
Methods were developed for the synthesis of 2-butylthio-2-oxo-1,3,2-oxazaphosphorinane, 2-butylthio-2-thioxo-1,3,2-dioxaphosphorinane, and 2-butylthio-2-thioxo-1,3,2-diazaphosphorinane, as well as of acyclicS-butylO-ethyl (diethylamido)phosphorothioates and-dithioates andS-butyl bis(diethylamido)phosphorodithioate. These compounds can serve as models of possible metabolites of cyclic compounds. Based on the data obtained in studies of the antiesterase activity of the resulting compounds and their synergistic activity in mixtures with permethrine, a possible mechanism ofin vitro andin vivo biological action of diheteraphosphorinanes was proposed. 相似文献
18.
Gary M. Coppola 《Journal of heterocyclic chemistry》1983,20(2):331-336
Reactions of 1,3-disubstituted-2,3-dihydro-1,3,2-benzodiazaphosphorin-4 (1 H)-one 2-oxides ( 1 ) with various electrophiles were investigated. The treatment of 1 with aldehydes in the absence of a basic catalyst directlyafforded alcohols 7a-h in good yield. The product from the reaction of 1 with chloral, on treatment with sodium hydride, resulted in the formation of a dichloroepoxide ( 8 ). When 1 was allowed to react with isocyanates or isothiocyanates in the presence of triethylamine, amides 10a-e and thioamide 11 were produced in good yield. Compounds 1a and 1b were readily halogenated on their phosphorus atom by treatment with either carbon tetrachloride or carbon tetrabromide and triethylamine. The P-chloro compound 12a reacted with ethanol to furnish the P-ethoxy derivative 13 and, in an attempt to react 12a with bis (2-chloroethyl) amine, anhydride 14 was formed in high yield. Spectral data for the majority of the products are also discussed. 相似文献
19.
I. V. Konovalova V. F. Mironov G. A. Ivkova E. R. Zagidullina A. T. Gubaidullin I. A. Litvinov M. A. Kurykin 《Russian Journal of General Chemistry》2005,75(4):549-560
2-R-benzo[e][1,3,2]dioxaphosphinin-4-ones react with perfluorodiacetyl under mild conditions to form relatively labile spirophosphoranes containing a 1,3,2-dioxaphosphole ring. These compounds gradually convert to more stable 2-R-4,5-bis(trifluoromethyl)-1,3,2λ5-dioxaphosphole 2-oxides and diastereometic 2-R-4-(trifluoroacetyl)-4-(trifluoromethyl)benzo[f][1,3,2λ5]dioxaphosphepine 2-oxides, whose structure was confirmed by means of NMR and IR spectroscopy. The structure of 4′,5′ -bis(trifluoromethyl)-4-oxo-2-(2,2,3,3-tetrafluoropropoxy)-2λ 5-spiro[benzo[e][1,3,2]dioxaphosphinine-2,2′-[1,3,2]dioxaphosphole] was confirmed by X-ray diffraction analysis.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 4, 2005, pp. 587–599.Original Russian Text Copyright © 2005 by Konovalova, Mironov, Ivkova, Zagidullina, Gubaidullin, Litvinov, Kurykin. 相似文献
20.
M. A. Pudovik S. A. Terent'eva I. A. Litvinov O. N. Kataeva V. A. Naumov A. N. Pudovik 《Russian Chemical Bulletin》1993,42(10):1706-1709
The reaction of 2-diethylamino-3-diethylaminomethyl-1,3,2-benzoxazaphospholine with functionally substituted alcohols and
phenols occurs with the cleavage of exocyclic P-N bond followed by N→P migration of the diethylaminomethyl group and formation
of imidophosphonate dimers. A similar reaction with polyhydroxy compounds (diethylene glycol, glycerol) results in symmetrical
and asymmetrical spirophosphoranes.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1781–1784, October, 1993. 相似文献