Microwave Irradiation in Organophosphorus Chemistry 1: The Michaelis-Arbuzov Reaction

Kiddle, James J.; Gurley, Alison F.

doi:10.1080/10426500008043680

Cited by 63 publications

(33 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[26] (Table 1, [27] ( Table 1, [28] ( Table 1, P NMR date were consistent with those previously reported. [29] Allyl diphenyl phosphinoxide [30] ( Table 1, P NMR and 13 C NMR data were consistent with those previously reported.…”

Section: General Procedures For Phosphine Oxides (Phosphinates or Phossupporting

confidence: 91%

Studies on the Efficient Generation of PhosphorusCarbon Bonds via a Rearrangement of P^III Esters Catalysed by Trimethylhalosilanes

Dąbkowski

Ozarek

Olejniczak

et al. 2009

Chemistry A European J

View full text Add to dashboard Cite

Halotrimethylsilanes Me(3)SiX (X = Br, I) catalyse rearrangements of tricoordinate phosphorus esters R'R''P-OR into the corresponding phosphoryl systems R'R''P(O)R. This provides a simple and efficient route to a variety of structures containing phosphorus-carbon bonds, under mild conditions and with good yields. The reaction mechanism was investigated in detail by (31)P NMR spectroscopy and independent synthesis of the reaction intermediates. It has been demonstrated that the primary products of this catalytic reaction are halogeno P(III) structures R'R''PX and silyl ethers ROSiMe(3) and that they subsequently react to give the corresponding phosphorus silyl esters-Me(3)SiOPR'R''-and alkyl halides RX. At higher temperatures these intermediates then react to form R'R''P(O)R compounds. This paper also features the surprising observation that when esters Ph(2)POR and halotrimethylsilanes Me(3)SiX (X = Br, I) are used in 2:1 ratio, phosphonium salts Ph(2)R(2)P(+)X(-) and trimethylsilyl diphenylphosphinate--Ph(2)P(O)OSiMe(3)--are formed as the major products. Experimental evidence indicates that the mechanisms of both reactions are fundamentally different from that of the Michaelis-Arbuzov reaction. Me(3)SiCl is not reactive and this paper explains why.

show abstract

Section: General Procedures For Phosphine Oxides (Phosphinates or Phossupporting

confidence: 91%

Studies on the Efficient Generation of PhosphorusCarbon Bonds via a Rearrangement of P^III Esters Catalysed by Trimethylhalosilanes

Dąbkowski

Ozarek

Olejniczak

et al. 2009

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…For TLC analysis, Alugram SIL G/UV 254 (Macherey-Nagel) plates were used. The N-aminophthalimide [27] and the phosphonates [28] were prepared by known procedures.…”

Section: Experimental Section Generalm Ethodsmentioning

confidence: 99%

Oxidative Aminoaziridination of 2‐Vinylfuran Derivatives as an Approach to Hexa‐2,5‐diene‐1,4‐dione Monohydrazones

2016

View full text Add to dashboard Cite

The oxidative addition of N-aminophthalimide to substituted2-vinylfurans provides monophthaloylhydrazones of (2Z)-hexa-2,5-diene-1,4-dione derivativesi nstead of 2-furylaziridines by proceeding through an aziridination of the endocyclic furan C=Cb ond followed by ar egio-and stereoselective rearrangement of the bicyclic intermediate. The formation of stable aziridines can then occur through the aziridination of the (E)-C=Cb ondo ft hese phthaloylhydrazones. Detailed structure elucidations and mechanistic considerations are provided.

show abstract

“…18 By contrast, microwave irradiation allows uniform heating and higher temperatures which has been demonstrated for phosphonates with small organic substituents at phosphorus. 19,20 In combining the beneficial features of the aryl and the alkyl based phosphonate ligands we set out to explore the microwave driven preparation of a biphenyl based bisphosphonate. Here we report a novel synthetic access to (C 6 H 4 PO(OiPr) 2 ) 2 under solvent free conditions in high yield, and its use as ligand for the construction of efficiently photoluminescent coordination polymers involving Eu, Tb, Dy cations along with their nonemissive Y analog.…”

mentioning

confidence: 99%

Facile access to efficiently luminescent Ln³⁺ phosphonic ester coordination polymers (Ln = Eu, Tb, Dy)

2017

View full text Add to dashboard Cite

show abstract

Microwave Irradiation in Organophosphorus Chemistry 1: The Michaelis-Arbuzov Reaction

Cited by 63 publications

References 24 publications

Studies on the Efficient Generation of PhosphorusCarbon Bonds via a Rearrangement of P^III Esters Catalysed by Trimethylhalosilanes

Studies on the Efficient Generation of PhosphorusCarbon Bonds via a Rearrangement of P^III Esters Catalysed by Trimethylhalosilanes

Oxidative Aminoaziridination of 2‐Vinylfuran Derivatives as an Approach to Hexa‐2,5‐diene‐1,4‐dione Monohydrazones

Facile access to efficiently luminescent Ln³⁺ phosphonic ester coordination polymers (Ln = Eu, Tb, Dy)

Contact Info

Product

Resources

About

Microwave Irradiation in Organophosphorus Chemistry 1: The Michaelis-Arbuzov Reaction

Cited by 63 publications

References 24 publications

Studies on the Efficient Generation of PhosphorusCarbon Bonds via a Rearrangement of PIII Esters Catalysed by Trimethylhalosilanes

Studies on the Efficient Generation of PhosphorusCarbon Bonds via a Rearrangement of PIII Esters Catalysed by Trimethylhalosilanes

Oxidative Aminoaziridination of 2‐Vinylfuran Derivatives as an Approach to Hexa‐2,5‐diene‐1,4‐dione Monohydrazones

Facile access to efficiently luminescent Ln3+ phosphonic ester coordination polymers (Ln = Eu, Tb, Dy)

Contact Info

Product

Resources

About

Studies on the Efficient Generation of PhosphorusCarbon Bonds via a Rearrangement of P^III Esters Catalysed by Trimethylhalosilanes

Studies on the Efficient Generation of PhosphorusCarbon Bonds via a Rearrangement of P^III Esters Catalysed by Trimethylhalosilanes

Facile access to efficiently luminescent Ln³⁺ phosphonic ester coordination polymers (Ln = Eu, Tb, Dy)