Zur Synthese von primären 1‐Aminocyclohexanphosphonsäurediestern und Folgeprodukten

Kochmann, Werner; Günther, Eberhard; Röthling, Thilo

doi:10.1002/j.0044-2402.1976.tb00118.x

Cited by 10 publications

(1 citation statement)

References 2 publications

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“…1 H NMR (250 MHz, CDCl 3 ):  = 0.92 (d, J = 6.1 Hz, 3 H), 1.22 (d, J = 6.2 Hz, 3 H), 1.26 (d, J = 6.2 Hz, 3 H), 1.32 (d, J = 6.2 Hz, 3 H), 4. 46 Diphenyl (Phenyl(phenylamino)methyl)phosphonate (4o) 35 Yield: 85% (353 mg); white solid; mp 152-153 °C (Lit. [35] mp 150-152 °C).…”

Section: Diethyl (2-(phenylamino)octan-2-yl)phosphonate (4k)mentioning

confidence: 99%

An Efficient One-Pot Synthesis of 1-Aminophosphonates

et al. 2022

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1-Aminophosphonates are valuable compounds with wide range applications in biological and industry. Various reaction conditions and catalysts have been reported for the synthesis of 1-aminophosphonates via three components (dialkylphos-phite+aldehyde+amine) or two component reaction (dialkylphos-phite+imine). We report here a solvent-free synthesis of 1-aminophosphonates under very mild reaction condition. Three component condensation reactions of dialkyl phosphite, carbonyl compound, and an amine gave 1-aminophosphonate in good to excellent yield under solvent- and catalyst-free condition at ambient temperature. Hydrophosphorylation of imines in the presence of dialkylphosphite under same condition gave also 1-aminophosphonates in good to excellent yield. These results showed that the reaction needs no to any catalyst or solvent for activation. It seems a tautomeric form of dialkylphosphite (as one of the components) catalysed the reaction. The reaction yield decreased using any solvent. In addition, a novel method will be reported for the synthesis of N-deprotected 1-aminophosphonates (analogues of 1-amino acids) from N-PMP 1-aminophosphonate in the presence of TCCA. To understand the activity of the dialkylphosphite under solvent free condition, the DFT calculations have provided insight into the basis of this activity.

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Section: Diethyl (2-(phenylamino)octan-2-yl)phosphonate (4k)mentioning

confidence: 99%

An Efficient One-Pot Synthesis of 1-Aminophosphonates

et al. 2022

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The Synthesis of Functionalized Phosphinic and Phosphonic Acids and their Derivatives. PartB: Diazo, Nitro and Amino Functionalized Acids

Edmundson¹

2009

Patai's Chemistry of Functional Groups

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Properties and Reactions of Phosphonic and Phosphinic Acids and their Derivatives

Edmundson¹

2009

Patai's Chemistry of Functional Groups

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Introduction The Role of the Phosphoryl ( P  Z )( Z = O , S , Se OR Te )Group Cleavage of the Phosphorus—Carbon Bond Reactions and Properties of the Carbon Ligands: The Functional Groups Reactions and Properties of the Carbon Ligands: The Carbon Skeleton Displacement Reactions of Non‐Carbon Ligands at Phosphorus

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Zur Synthese von primären 1‐Aminocyclohexanphosphonsäurediestern und Folgeprodukten

Cited by 10 publications

References 2 publications

An Efficient One-Pot Synthesis of 1-Aminophosphonates

An Efficient One-Pot Synthesis of 1-Aminophosphonates

The Synthesis of Functionalized Phosphinic and Phosphonic Acids and their Derivatives. PartB: Diazo, Nitro and Amino Functionalized Acids

Properties and Reactions of Phosphonic and Phosphinic Acids and their Derivatives

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