Microwave Irradiation as a Useful Tool in Organophosphorus Syntheses

Keglevich, György; Szekrényi, Anna; Kovács, Rita; Grűn, Alajos

doi:10.1080/10426500902948003

Cited by 13 publications

(6 citation statements)

References 18 publications

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“…Cycloadducts 2a and 2b were identified by earlier described 31 P NMR spectral data. 18,19 According to earlier results, using a 1:1.2 molar ratio of dihydrophosphi- 6 ]. It can be seen that the cycloadditions became faster in the IL used than in toluene and 100 • C is more appropriate than 60 • C. Preparative yields of 2a and 2b were 83% and 70%, respectively (Table 1, entries 3 and 6).…”

Section: Resultsmentioning

confidence: 97%

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Diels–Alder Cycloadditions of 1,2-Dihydrophosphinine Oxides and Fragmentation-Related Phosphorylations with 2-Phosphabicyclo[2.2.2]Octadiene Oxides Under Green Chemical Conditions—The Role of Microwave and Ionic Liquids

Keglevich

Kovács

Drahos

2011

Phosphorus, Sulfur, and Silicon and the Related Elements

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R 2 P Y O Cl R 1 P R 2 O Y Cl R 1 + P Y Me O O R 2 P Y O Cl R 1 CO 2 Me CO 2 Me + OH R R R 1 R 2 H Me Me H Y = Ph, EtO R = Me, H Abstract The effect of the use of microwave (MW) and solvents including ionic liquids on the Diels-Alder reaction of 1,2-dihydrophosphinine oxides (1) and fragmentation-related phosphorylation of phenols with 2-phosphabicyclo[2.2.2]octadiene oxides (4) was studied. The MW-assisted Diels-Alder reaction of dihydrophosphinine oxides (1) with N-phenylmaleimide may be advantageous to carry out in [bmim][BF 4 ] due to shorter reaction times, but the dimerization of the double-bond isomers (A and B) of the dihydrophosphinine oxides (1) may be best accomplished under MW in the absence of any solvent. The fragmentation-related phosphorylations may also be carried out under MW, which with the P-phenyl precursor (4a) became more efficient in [bmim][BF 4 ].

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Section: Resultsmentioning

confidence: 97%

“…The MW technique was utilized in solventless Diels-Alder, 5,6 inverse Wittig, 6,7 and Kabachnik-Fields reactions, 6,8 as well as in the direct esterification of phosphinic acids. 9,10 ILs were useful in Arbuzov reactions, 11 but in certain cases, these reactions led to unexpected results.…”

Section: Introductionmentioning

confidence: 99%

Diels–Alder Cycloadditions of 1,2-Dihydrophosphinine Oxides and Fragmentation-Related Phosphorylations with 2-Phosphabicyclo[2.2.2]Octadiene Oxides Under Green Chemical Conditions—The Role of Microwave and Ionic Liquids

Keglevich

Kovács

Drahos

2011

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…Organophosphorus compounds including P ‐heterocycles may find applications in synthetic organic chemistry as reactants, solvents (ionic liquids), catalysts, P ‐ligands in complexes, and due to their biological activity also as drugs and plant protecting agents . The utilization of MW irradiation in organophosphorus chemistry is a relatively new field …”

Section: Introductionmentioning

confidence: 99%

The Impact of Microwaves on Organophosphorus Chemistry

Keglevich

2018

The Chemical Record

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A personal account on the pioneering results on microwave (MW)-assisted organophosphorus syntheses obtained in the last decade is presented. The broad spectrum of the reactions studied exemplifies the advantages of the MW technique as a green tool regarding efficiency and the simplification of catalyst systems. Theoretical calculations for a few typical models helped us to explore the scope and limitations of the application of MW irradiation.

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“…Several green chemical synthetic approaches using the KF reaction are reported in solvent‐ and catalyst‐free conditions , solvent‐free under MWI using heterocyclic amines, oxo‐component, and >P(O)H species . All of these reports are based on few model reactions .…”

Section: Introductionmentioning

confidence: 99%

An Efficient Green Synthesis of a New Class of α‐Aminophosphonates under Microwave Irradiation Conditions in the Presence of PS/PTSA

Gangireddy

Chinthaparthi

Mudumala

et al. 2014

Heteroatom Chemistry

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The present work focuses on the study of catalytic activity of polystyrene‐supported p‐toluenesulfonic acid (PS/PTSA) and the synthesis of α‐aminophosphonates from the Kabachnik–Fields (KF) reaction under microwave irradiation in solvent‐free conditions. Recently, the catalytic activity of PS/PTSA was tested with good yields. This procedure is the simplest, most straightforward, environment friendly method for the synthesis of α‐aminophosphonates from simple to different substituted aldehyde substrates. Furthermore, this catalyst can be recovered and reused without loss of its catalytic activity.

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Microwave Irradiation as a Useful Tool in Organophosphorus Syntheses

Abstract: Application of the microwave technique offers advantages in organophosphorus chemistry, such as in the Kabachnik-Fields reaction, in Diels-Alder cycloadditions, in an inverse Wittig-type reaction, and in fragmentation-related phosphorylations.

Cited by 13 publications

References 18 publications

Diels–Alder Cycloadditions of 1,2-Dihydrophosphinine Oxides and Fragmentation-Related Phosphorylations with 2-Phosphabicyclo[2.2.2]Octadiene Oxides Under Green Chemical Conditions—The Role of Microwave and Ionic Liquids

Diels–Alder Cycloadditions of 1,2-Dihydrophosphinine Oxides and Fragmentation-Related Phosphorylations with 2-Phosphabicyclo[2.2.2]Octadiene Oxides Under Green Chemical Conditions—The Role of Microwave and Ionic Liquids

The Impact of Microwaves on Organophosphorus Chemistry

An Efficient Green Synthesis of a New Class of α‐Aminophosphonates under Microwave Irradiation Conditions in the Presence of PS/PTSA

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