Studies of the Synthesis of Diethyl Cyclopropylphosphonate and Its Thio and Seleno Analogs

Zafrani, Yossi; Chen, Ravit; Ashkenazi, Nissan; Segall, Yoffi

doi:10.1080/00397910701845332

Cited by 3 publications

(1 citation statement)

References 35 publications

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“…Cyclopropylamine 2 and cyclopropylmethylamine 3 were purchased from the Aldrich Company and used without further purification. 2-Chloroethylphosphine, cyclopropyldiethylphosphonate, cyclopropylmethylphosphine, cyclopropylphosphine-borane, aziridine, aziridine-borane, and methylamine-borane were prepared as previously reported. Phosphirane 4 , cyclopropylphosphine 5 , and cyclopropylamine-borane 8 have been prepared as described in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Differences Between Amine- and Phosphine-Boranes: Synthesis, Photoelectron Spectroscopy, and Quantum Chemical Study of the Cyclopropylic Derivatives

et al. 2010

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Borane complexes of aziridine, phosphirane, cyclopropylamine, cyclopropylphosphine, cyclopropylmethylamine, and cyclopropylmethylphosphine have been prepared by the reaction at low temperatures of a borane complex or diborane on the free phosphine or amine. The products characterized by NMR spectroscopy and mass spectrometry have then been investigated by photoelectron spectroscopy and B3LYP/aug-cc-pVTZ quantum chemical study. The complexation led to rotamers with structures similar to the ones of the corresponding free systems. The main geometry change with the complexation is the P-C bond elongation and the N-C bond shortening, which can be rationalized by the charge transfer attached to the electron donation. The calculated relative stability order of the conformers changes with the complexation only in the case of cyclopropylamine. The calculated complexation energies are higher for the amines, in accord with the differences observed in the flash vacuum thermolysis of methylamine-, methylphosphine-, and aziridine-borane. The photoelectron spectra indicate essential differences between the amines and phosphines toward borane complexation. The dative bond is more stable in the studied amine-boranes than in phosphine-boranes, while the sigma(B-H) orbitals are more stable in the latter compounds. The enthalpy of the hydrogen release reaction of aziridine-borane is almost thermoneutral, indicating the potential of this complex as recyclable hydrogen storage material.

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Section: Methodsmentioning

confidence: 99%

Differences Between Amine- and Phosphine-Boranes: Synthesis, Photoelectron Spectroscopy, and Quantum Chemical Study of the Cyclopropylic Derivatives

et al. 2010

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Visible‐Light‐Promoted Redox‐Neutral Cyclopropanation Reactions of α‐Substituted Vinylphosphonates and Other Michael Acceptors with Chloromethyl Silicate as Methylene Transfer Reagent

et al. 2018

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The alkene cyclopropanation with chloromethyl silicate as a methylene transfer reagent has been accomplished via visible‐light‐mediated redox‐neutral catalysis. This method features broad functional group tolerance and mild conditions. In addition to α‐substituted vinylphosphonates, a range of Michael acceptors including α,β‐unsaturated acrylate, ketone, amide and sulfone are suitable substrates for this photocatalytic cyclopropanation. An application of this protocol to the cyclopropanation of estrone derivative is also presented.magnified image

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ChemInform Abstract: Synthesis of Diethyl Cyclopropylphosphonate and Its Thio and Seleno Analogues.

et al. 2008

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Studies of the Synthesis of Diethyl Cyclopropylphosphonate and Its Thio and Seleno Analogs

Cited by 3 publications

References 35 publications

Differences Between Amine- and Phosphine-Boranes: Synthesis, Photoelectron Spectroscopy, and Quantum Chemical Study of the Cyclopropylic Derivatives

Differences Between Amine- and Phosphine-Boranes: Synthesis, Photoelectron Spectroscopy, and Quantum Chemical Study of the Cyclopropylic Derivatives

Visible‐Light‐Promoted Redox‐Neutral Cyclopropanation Reactions of α‐Substituted Vinylphosphonates and Other Michael Acceptors with Chloromethyl Silicate as Methylene Transfer Reagent

ChemInform Abstract: Synthesis of Diethyl Cyclopropylphosphonate and Its Thio and Seleno Analogues.

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