PREPARATION DE l'ACIDE AMINOMETHYLPHOSPHONIQUE Α-Dideuterie

Berté-Verrando, Sylvie; Nief, François; Et, Carl Patois; Savignac, Philippe

doi:10.1080/10426509508027368

Cited by 15 publications

(18 citation statements)

References 5 publications

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“…The nucleophilic azidation of chloromethylphosphonic diesters [42] was studied by Savignac et al [46]. They obtained an almost quantitative yield of bis-(2,2,2-trifluoroethyl) azidomethylphosphonate 44a in the reaction of bis-(2,2,2-trifluoroethyl) chloromethylphosphonate 43a with sodium azide in DMSO at 90 o C. Analogously, bis-(2,2,2-trifluoroethyl) dideuterioazidomethylphosphonate (not shown) was obtained from bis-(2,2,2-trifluoroethyl) dideuteriochloromethylphosphonate.…”

Section: Nucleophilic Substitution Of -Halogeno Derivativesmentioning

confidence: 99%

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Synthesis and Reactivity of Azidoalkylphosphonates, -Phosphinates and -Phosphine Oxides

Gajda

2007

COC

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This review will focus on the synthesis of -and -azidoalkylphosphonic and -phosphinic acids, -phosphine oxides and their derivatives as well as their reactions utilizing the azido group and/or phosphyl group. In the first part of this review synthetic routes to such azides will be reviewed. Generally, these compounds are achieved via nucleophilic substitution of hydroxy derivatives of phosphonates, -phosphinates, and -phosphine oxides by the Mitsunobu protocol or by the displacement of their sulfonates or halogen derivatives with azides. The ring-opening of phosphorus-containing oxiranes or cyclic vicinal sulfates with azides will also be discussed. Electrophilic azidation of the corresponding phosphorus-stabilized carbanions has also been described. In the second part of the review emphasis will be placed on the application of azido derivatives in organic synthesis. 1,3-Dipolar cycloaddition is an excellent tool in the construction of fivemembered heterocycles. Therefore, the formation of 1,2,3-triazoles from alkynes, enamines and 2-oxoalkylidenetriphenylphosphoranes will be discussed. Hence, the azido group is easily converted into amine, and phosphorus-containing azides can be considered to be azide-masked equivalents of amino derivatives or their N-protected derivatives. The application of such azides in the synthesis of phosphorus analogs of amino acids will be discussed. The synthesis of carbodiimides, imines, isothiocyanates and phosphonodipeptides has also been reviewed.

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Section: Nucleophilic Substitution Of -Halogeno Derivativesmentioning

confidence: 99%

“…This process can be extended to the synthesis of 1-aminocycloalkylphosphonates [59], -hydroxy functionalized aminophosphonates [31][32][33], aminodideuteriomethylphosphonates or -phosphinates [46,49,62] and 1-amino-1-deoxy-1-phosphylglycerols [37].…”

Section: -Aminoalkylphosphonates and -Phosphinatesmentioning

confidence: 99%

Synthesis and Reactivity of Azidoalkylphosphonates, -Phosphinates and -Phosphine Oxides

Gajda

2007

COC

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“…44 The removal of the hydrogen chloride formed in the reaction is achieved with a stream of dry air, 45 appliance of occasional slight vacuum, 46 or constant water pump vacuum (for diols only). 47 However, the addition of a tertiary amine (pyridine 48,49 and triethylamine [50][51][52][53][54][55] ) remains the most widely used method to trap the hydrogen chloride. The direct addition of sodium alcoholate 56 is also a useful synthetic method.…”

Section: Chloromethylphosphonatesmentioning

confidence: 99%

The Synthesis of Dialkyl α-Halogenated Methylphosphonates

Waschbüsch¹,

Carran²,

Marinetti³

et al. 1997

Synthesis

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“…However, the undesirable alkylation reaction (route b) can be avoided by using phosphonate esters bearing electron withdrawing groups (R = CCl 3 or CF 3 ). 102 The attack of the nucleophilic reagent on the ester carbon atom is thus slowed down. Alkylation can also be avoided by using phosphonamides instead of phosphonate esters.…”

Section: Diethyl Chloromethylphosphonate : Chlorine Substitutionmentioning

confidence: 99%

“…So it is common to find the introduction of a phosphonic acid group in place of the normal carboxylic acid group.This analogy has induced a lot of work devoted to the nucleophilic amination of 1, the aminating agents being NH 4 OH, 100 R 1 R 2 NH 101 or NaN 3 . 102 The first method for the preparation of diethyl aminomethylphosphonate involved the amination of 1 with a 25 % aqueous solution of NH 3 in a sealed tube at 150 °C. 100 An almost quantitative yield of azidophosphonate results from reaction of bis(trifluoroethyl) chloromethylphosphonate 56 with sodium azide in DMSO at 90 °C.…”

Section: Amino Derivativesmentioning

confidence: 99%