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Sagadeev, V. V.; Sagadeev, E. V.; Kafiatullin, R. A.; Sagadeev, V. I.

doi:10.1023/a:1016834316440

Cited by 4 publications

(17 citation statements)

References 1 publication

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“…The possible acyclic structure shown in Figure 3, MeAP(O)(OCH 2 CH 2 OCH 2 CH 2 OH) 2 , as one of the proposed structure for the isolated compound was ruled out not only because of the M þ peak in the mass spectrum but also because of the four 13 C peaks needed for the OCH 2 carbon atoms of this phosphonate. The 13 C{ 1 H} NMR and mass spectral data of this phosphonate was quite different from the data obtained for the isolated phosphonate.…”

Section: Resultsmentioning

confidence: 99%

“…The 13 C{ 1 H} NMR spectrum of the reaction mixture was similar to the products observed from method one. The three doublet peaks in 13 C NMR spectrum of the reaction mixture, in the region 10-15 ppm, corresponding to CH 3 P(O) carbon atoms, are indicative of the presence of three methylphosphonates as products.…”

Section: Resultsmentioning

confidence: 99%

“…The NMR and mass spectroscopic data for this fraction were found to be in agreement with the fivemembered ring methylphosphonate II. A doublet and a singlet at 11.63 and 66.68 ppm in the 13 The mass spectrum of II is presented in Figure 2(d). The molecular ion peak at m/z 122, a peak at m/z 28 corresponding to the CH 2 ACH 2 fragment and a peak at m/z 96 for MeP(O)(OH) 2 are all supporting data for the proposed structure II.…”

Section: Resultsmentioning

confidence: 99%

“…To estimate the approximate percentages of compounds I and II obtained by each method, the 13 P signal intensities were considered. It was determined that I and II have been formed in 15:1 and 10:1 mole ratios by using method one and two, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…A search in the literature indicates that although compound I was reported in 1957 [9] from ethylene glycol and methylphosphonic dichloride, there also have been some reports, mostly theoretical, for compound II [10][11][12][13]. Neither of these cyclic phosphonates has been completely spectroscopically identified.…”

Section: Introductionmentioning

confidence: 99%

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Concurrent formation of five and eight‐membered heterocyclic methylphosphonates in cyclization reactions from diethyleneglycole

Moghimi

Rafiei

Baghaie

et al. 2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Two methodologies have been investigated for the preparation of heterocyclic methylphosphonate using diethyleneglycole and either MPDC or DMMP as the bifunctional group starting materials needed for cyclization reactions. In addition to the eight-membered ring methylphosphonate I the fivemembered ring methylphosphonate II was unexpectedly found to be formed during the cyclization reactions. This small-size cyclic methylphosphonate may have been generated from an intramolecular cyclization reaction by the nucleophilic attack of the ether oxygen atom of the intermediate MeAP(O)(X)OCH 2 CH 2 AOACH 2 CH 2 OH (X ¼ Cl or OMe). The resulting cyclic phosphonates were purified and characterized by NMR and mass spectroscopy.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Concurrent formation of five and eight‐membered heterocyclic methylphosphonates in cyclization reactions from diethyleneglycole

Moghimi

Rafiei

Baghaie

et al. 2009

Journal of Heterocyclic Chem

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Polynomial Dependence for the Calculation of Vaporization Enthalpies of Organophosphorus Compounds

2005

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Enthalpies of vaporization of organic phosphorus compounds are related to the normal-pressure boiling points through a polynomial dependence. Each class of organophosphorus compounds is characterized by its own specific parameters of the general dependence. The polynomial dependences may be used for the calculation of vaporization enthalpies of organophosphorus compounds with different modes of phosphorus coordination.Most of the known experimental enthalpies of vaporization of organic three-and four-coordinate phosphorus compounds were determined by two methods. The first of these is based on the Clapeyron-Clausius equation [1]:where p is the vapor pressure; H vap is the enthalpy of vaporization (kJ/mol), R is the universal gas constant, T is the absolute temperature, and C is the integration constant.The second method is based on the Solomonov equation [2,3]:where H dis is the enthalpy of dissolution of a substance (kJ/mol), and MR D is its molecular refraction. However, both these procedures for experimental determination of H°v ap of organophosphorus compounds are not free from a number of disadvantages which could appreciably restrict the scope of their application in practice. For example, the use of the Clapeyron-Clausius equation is limited due to high boiling points of organic phosphorus compounds which therefore tend to decompose on heating. Determination of the enthalpies of dissolution of organophosphorus compounds in inert organic solvents, which are necessary for the calculation of vaporization enthalpies by the Solomonov equation, is not always possible due to insufficient stability of these compounds to oxidation on exposure to atmospheric oxygen and to hydrolysis in the presence of traces of water. Taking into account the above stated, theoretical methods for the calculation of vaporization enthalpies of organophosphorus compounds become more important. In particular, the additivity scheme involving group contributions [4] can be used for this purpose:Here, m i is the number of similar fragments in a molecule, and X i is an increment characterizing the group contribution of an ith fragment. However, the calculation of standard enthalpies of vaporization of organic phosphorus compounds according to the additivity scheme may be difficult, for there are very limited published data on the contributions of phosphorus-containing groups to H°v ap . The relevant data have been reported in a few articles [5,6]. Moreover, the possibility for calculating contributions of phosphorus-containing groups to the enthalpy of vaporization of organophosphorus compounds is limited due to shortage of experimental data and, in some cases, large errors in experimental determination.In the recent time, attempts were made [7-10] to calculate enthalpies of vaporization of three-coordinate

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Calculation of Fundamental Thermochemical Parameters of Phosphoranes by the Additivity Scheme

2005

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Cited by 4 publications

References 1 publication

Concurrent formation of five and eight‐membered heterocyclic methylphosphonates in cyclization reactions from diethyleneglycole

Concurrent formation of five and eight‐membered heterocyclic methylphosphonates in cyclization reactions from diethyleneglycole

Polynomial Dependence for the Calculation of Vaporization Enthalpies of Organophosphorus Compounds

Calculation of Fundamental Thermochemical Parameters of Phosphoranes by the Additivity Scheme

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