CHLORINE FREE SYNTHESIS OF ORGANOPHOSPHORUS COMPOUNDS BASED ON THE FUNCTIONALIZATION OF WHITE PHOSPHORUS (P<sub>4</sub>)

Abdreimova, Rumiya R.; Akbayeva, Dina N.; Polimbetova, G. S.; Caminade, Anne‐Marie; Majorals, Jean-Pierre

doi:10.1080/10426500008045007

Cited by 16 publications

(10 citation statements)

References 7 publications

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“…27 Thus, we postulate that the starting complex [Cu 3 L 3 ] decomposes with the formation of the Cu II complex [Cu{tBuNHC(S)NP(O)(OiPr) 2 -N,S} 2 ], which is unstable in solutions and further decomposes. A signal for (iPrO) 2 P(O)OH at 2-3.5 ppm (d P = 2.98 ppm) 28 was observed in 31 P{ 1 H} NMR spectra of reaction mixtures, though complex [Cu 3 L 3 ] could be isolated quantitatively in a shorter time, e.g. 1.5 d (yield 98%).…”

Section: Resultsmentioning

confidence: 99%

Aerial oxidation of tetrahydrofuran to 2-hydroxotetrahydrofuran in the presence of a trimeric CuI complex [Cu3L3] (HL = tBuNHC(S)NHP(S)(OiPr)2) and trapping of the unstable product at recrystallization

et al. 2010

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The reaction of the potassium salt of N-thiophosphorylated thiourea tBuNHC(S)NHP(S)(OiPr) 2 (HL) with Cu(NO 3 ) 2 in aqueous EtOH leads to the trinuclear [Cu 3 (tBuNHC(S)NP(S)(OiPr) 2 -S,S 0 ) 3 ] ([Cu 3 L 3 ]) complex. It was established that [Cu 3 L 3 ] provokes the aerobic oxidation of tetrahydrofuran to 2-hydroxotetrahydrofuran and traps the latter at crystallization.Scheme 1 Mono-oxygenation of THF.

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Section: Resultsmentioning

confidence: 99%

Aerial oxidation of tetrahydrofuran to 2-hydroxotetrahydrofuran in the presence of a trimeric CuI complex [Cu3L3] (HL = tBuNHC(S)NHP(S)(OiPr)2) and trapping of the unstable product at recrystallization

et al. 2010

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“…A radical mechanism is suggested for both the stoichiometric and the catalytic oxidative hydroxydation, alkoxydation, and phenoxidation of P 4 promoted by peroxides both under aqueous biphasic conditions and in organic solutions. The catalytic oxidative alkoxylations of P 4 with oxygen were reported using Pd(II) and Ru(II) catalyst and a co-oxidant such as CuCl 2 , NaNO 2 , or FeCl 3 , leading to trialkylphosphates (RO) 3 P(O) and dialkylphosphites (RO) 2 P(O)H …”

Section: Activation and Degradation Of P4 Phosphorus By Main Group El...mentioning

confidence: 99%

P₄Activation by Main Group Elements and Compounds

2010

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Contents 1. Introduction 4236 2. The Stability of P 4 Phosphorus with Respect to Its Allotropes and Neutral Polyphosphorus Species 4237 2.1. Allotropic Modifications of Phosphorus 4237 2.2. Stability of Neutral Polyphosphorus Species 4238 3. General Trends of P 4 Phosphorus Activation 4239 3.1. General Remarks 4239 3.2. Degradation of P 4 Phosphorus by Nucleophiles under Maintenance of P n Structural Moieties 4241 4. Activation and Degradation of P 4 Phosphorus by Main Group Elements and Compounds 4243 4.1. Activation of P 4 Phosphorus by Group 1 and 2 Elements and Compounds 4243 4.2. Activation of P 4 Phosphorus by Group 13 Element Compounds 4245 4.3. Activation and Degradation of P 4 Phosphorus by Group 14 Element Compounds 4246 4.4. Activation and Degradation of P 4 Phosphorus by Group 15 Element Compounds 4250 4.5. Activation and Degradation of P 4 Phosphorus by Group 16 and 17 Element Compounds 4251 5. Abbreviations 4252 6. Acknowledgments 4253 7. References 4253

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“…Besides the two main routes mentioned above, there are a few less important methods for the synthesis of dialkyl H -phosphonates. Such protocols are the oxidative reaction of elemental phosphorus with alcohols ( Scheme 3 a) [ 55 , 56 , 57 , 58 , 59 , 60 ] and the Ni-catalyzed oxidation of hypophosphorous esters ( Scheme 3 b) [ 61 ].…”

Section: Introductionmentioning

confidence: 99%

Continuous Flow Alcoholysis of Dialkyl H-Phosphonates with Aliphatic Alcohols

et al. 2018

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The continuous flow alcoholysis of dialkyl H-phosphonates by aliphatic alcohols in the absence of a catalyst was elaborated using a microwave (MW) reactor equipped with a flow cell. By the precise control of the reaction conditions, the synthesis could be fine-tuned towards dialkyl H-phosphonates with two different and with two identical alkyl groups. In contrast to the “traditional” batch alcoholysis, flow approaches required shorter reaction times, and the products became available at a larger scale.

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CHLORINE FREE SYNTHESIS OF ORGANOPHOSPHORUS COMPOUNDS BASED ON THE FUNCTIONALIZATION OF WHITE PHOSPHORUS (P₄)

Cited by 16 publications

References 7 publications

Aerial oxidation of tetrahydrofuran to 2-hydroxotetrahydrofuran in the presence of a trimeric CuI complex [Cu3L3] (HL = tBuNHC(S)NHP(S)(OiPr)2) and trapping of the unstable product at recrystallization

Aerial oxidation of tetrahydrofuran to 2-hydroxotetrahydrofuran in the presence of a trimeric CuI complex [Cu3L3] (HL = tBuNHC(S)NHP(S)(OiPr)2) and trapping of the unstable product at recrystallization

P₄Activation by Main Group Elements and Compounds

Continuous Flow Alcoholysis of Dialkyl H-Phosphonates with Aliphatic Alcohols

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CHLORINE FREE SYNTHESIS OF ORGANOPHOSPHORUS COMPOUNDS BASED ON THE FUNCTIONALIZATION OF WHITE PHOSPHORUS (P4)

Cited by 16 publications

References 7 publications

Aerial oxidation of tetrahydrofuran to 2-hydroxotetrahydrofuran in the presence of a trimeric CuI complex [Cu3L3] (HL = tBuNHC(S)NHP(S)(OiPr)2) and trapping of the unstable product at recrystallization

Aerial oxidation of tetrahydrofuran to 2-hydroxotetrahydrofuran in the presence of a trimeric CuI complex [Cu3L3] (HL = tBuNHC(S)NHP(S)(OiPr)2) and trapping of the unstable product at recrystallization

P4Activation by Main Group Elements and Compounds

Continuous Flow Alcoholysis of Dialkyl H-Phosphonates with Aliphatic Alcohols

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CHLORINE FREE SYNTHESIS OF ORGANOPHOSPHORUS COMPOUNDS BASED ON THE FUNCTIONALIZATION OF WHITE PHOSPHORUS (P₄)

P₄Activation by Main Group Elements and Compounds