- HIV-1 non-nucleoside reverse transcriptase inhibitors: Incorporation of benzylphosphonate moiety for solubility improvement
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Benzylphosphonates of 5'-norcarbocyclic analogue of 2',3'-dideoxy-2',3'-didehydrouridine and its N3-benzyl derivatives with different substituents at the phosphorus atom were designed and synthesized in attempt to improve solubility of potentia
- Matyugina, Elena S.,Valuev-Elliston, Vladimir T.,Chizhov, Alexander O.,Kochetkov, Sergei N.,Khandazhinskaya, Anastasia L.
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- REACTIVE FLAME RETARDANT AND FLAME-RETARDANT RESIN PROCESSED ARTICLE
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Disclosed is a reactive flame retardant which provides a resin with excellent flame retardance even when it is added in a small amount while being prevented from bleedout. Also disclosed is a flame-retardant resin processed article obtained by using such a reactive flame retardant. An organophosphorus compound represented by the general formula (I) below, wherein at least one or more of X1-X3 represent a group containing phosphorus and having a terminal unsaturated group, is used as a reactive flame retardant which is reactive with resins. A flame-retardant resin processed article can be obtained by solidifying the resin composition containing the organophosphorus compound and then reacting it through heating or application of radiation.
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- Diastereoselective synthesis of α,α′-disubstituted β-ketophosphonates derivatives as building blocks for automated syntheses
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A convenient and efficient synthesis of α,α′- disubstituted β-ketophosphonic derivatives in good to excellent de's and yields has been achieved by α-acylation followed by diastereoselective α-alkylation of chiral 5-membered cyclic phosphonamidates.
- Pirat, Jean-Luc,Marat, Xavier,Clarion, Ludovic,Van Der Lee, Arie,Vors, Jean-Pierre,Cristau, Henri-Jean
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p. 2626 - 2637
(2007/10/03)
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- Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates
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Chiral, non-racemic α-hydroxyphosphonates have been prepared in high enantiomeric excess (96-98% ee), via stereoselective oxaziridine-mediated hydroxylation of diallyl benzylphosphonates. The enantiomeric purity and absolute configuration of the α-hydroxy
- Skropeta, Danielle,Schmidt, Richard R.
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p. 265 - 273
(2007/10/03)
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- Preparation of chiral α-monofluoroalkylphosphonic acids and their evaluation as inhibitors of protein tyrosine phosphatase 1B
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Enantiomerically pure α-monofluoroalkylphosphonic acids 4-9 were synthesized by diastereoselective electrophilic fluorination of α-carbanions of asymmetric phosphonamidates bearing (-)-ephedrine as a chiral auxiliary. The diastereomeric excess of the fluo
- Kotoris, Christopher C.,Wen, Wcndy,Lough, Alan,Taylor, Scott D.
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p. 1271 - 1281
(2007/10/03)
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- Electronic effects on the Z(cis)-selectivity of Horner-Wadsworth-Emmons olefination reaction
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Various phosphorates have been synthesized to study the Horner-Wadsworth-Emmons olefination reaction. The phosphoryl stabilised carbanion resulting from phosphonates, carrying electron withdrawing groups attached to phosphorus atom, has been reacted with a variety of aldehydes at - 78°C leading to Z(cis) selective olefination.
- Mahipal Reddy,Raj Gopal,Jayathirtha Rao
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p. 312 - 317
(2007/10/03)
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- Photoresolution of an axially chiral bicyclo[3.2.1]octan-3-one: Phototriggers for a liquid crystal-based optical switch
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The axially chiral ketones 8-(phenylmethylene)bicyclo[3.2.1]octan-3-one (1) and 3-(phenylmethylene)bicyclo[3.2.1]octan-8-one (2) were prepared and investigated for suitability as a chiroptical trigger in a liquid crystal-based optical switch. Irradiation
- Zhang,Schuster
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p. 7192 - 7197
(2007/10/03)
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- Easy preparation of alkylphosphonyl dichlorides
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Phosphonic acid esters bearing an alkyl, halogen or carboxylate substituent on the α-carbon are readily converted into the parent phosphonic dichlorides when treated with a mixture of 2.5 eq of phosphorus pentachloride and 1.3 eq of phosphorus oxychloride.Keywords - phosphonates / chlorination / phosphorus pentachloride / phosphorus oxychloride / phosphonyl dichloride
- Patois, C.,Berte-Verrando, S.,Savignac, P.
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p. 485 - 487
(2007/10/02)
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- The mild preparation of synthetically useful phosphonic dichlorides: Application to the synthesis of cyclic phosphonic diesters and diamides
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A very mild method for the preparation of synthetically useful phosphonic dichlorides has been developed and its application toward the synthesis of 2-alkyl-2-oxo-1,3,2-dioxophosphorinanes and 1,3-dimethyl-2-alkyl-2-oxo-1,3,2-diazaphospholidines is reported.
- Stowel,Ueland,McClard
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p. 3261 - 3262
(2007/10/02)
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- EXPEDIENT AND HIGH-YIELD SYNTHESIS OF ALKYLPHOSPHONYL DICHLORIDES UNDER MILD, NEUTRAL CONDITIONS: REACTION OF BIS(TRIMETHYLSILYL)ALKYL PHOSPHONATES WITH OXALYL CHLORIDE/DIMETHYLFORMAMIDE
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Structurally variant bis(trimethylsilyl)alkyl phosphonates were converted in high yields (80-88percent, distilled) to the corresponding phosphonyl dichlorides upon reaction with (COCl)2/DMF.
- Bhongle, Nandkumar N.,Notter, Robert H.,Turcotte, Joseph G.
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p. 1071 - 1076
(2007/10/02)
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- A MILD AND FACILE SYNTHESIS OF ALKYL- AND ARYLPHOSPHONYL DICHLORIDES UNDER NEUTRAL CONDITIONS. REACTION OF BIS(TRIMETHYLSILYL) PHOSPHONATES WITH PCl5
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Bis(trimethylsilyl) phosphonates, which are prepared from the dialkyl esters with chlorotrimethylsilane/sodium iodide, are transformed in high yields into the corresponding phosphonyl dichlorides on the treatment with phosphorus pentachloride under mild and neutral conditions.
- Morita, Tsuyoshi,Okamoto, Yoshiki,Sakurai, Hiroshi
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p. 435 - 438
(2007/10/02)
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- Process for the preparation of phosphonic acid dihalides
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A process for the preparation of phosphonic acid dihalides of the formula EQU1 IN WHICH R is α, β-unsaturated alkyl, α, β-unsaturated alkyl, phenyl or benzyl and may be further substituted, which comprises reacting corresponding phosphonic or pyrophosphonic acids or their functional derivatives with acid halides of the formula (CO)n Hal2 where n is 1 or 2.
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- Process for the preparation of phosphonic acid dihalides
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Process for preparing phosphonic acid dihalides of the formula EQU1 wherein R is alkyl of 1 to 18 carbon atoms, cycloalkyl of 4 to 8 carbon atoms, alkenyl of 2 to 18 carbon atoms, phenyl, phenalkyl or alkyl-phenyl of 7 to 8 carbon atoms, phenyl, phenalkyl or alkyl-phenyl of 7 to 8 carbon atoms, all radicals R optionally being substituted by chlorine, bromine, cyano or lower acyloxy, and wherein X is halogen such as 2-chloroethane phosphonic acid dichloride, by reacting phosphonic or thio-phosphonic acids of the formula EQU2 wherein Y is oxygen or sulfur, their salts or functional derivatives, with acid halides of the formula wherein X is chlorine or bromine and n is 1 or 2, in the presence of 0.2 - 5% or in the presence of 0.01 to 0.2% by weight of 1. compounds containing at least one tri- to pentavalent nitrogen or phosphorus atom, which in the case of nitrogen is bound with 1 to 4, in the case of phosphorus with at least 3 valences to organic radicals having up to 20 carbon atoms, two of these valences optionally forming a double bond, or 2. mono-di- or tribasic organic or inorganic fully amidated acids or tri- or pentavalent phosphorus, the N atom of which optionally being substituted by aliphatic radicals having up to 20 carbon atoms, and the organic radicals of which contain up to 20 carbon atoms, If required, in the presence of an inert solvent.
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