Synthesis and Properties of Phosphorus Ylides Containing Fluorine Atoms Bonded to Phosphorus

Kolodiazhnyi, Oleg I.; Schmutzler, Reinhard

doi:10.1055/s-2001-15133

Cited by 25 publications

(11 citation statements)

References 27 publications

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“…The 31 Р-NMR spectra of 2-fluorooxaphosphetanes 17 present doublets with 800 Hz 1 JРF constants in the high magnetic field of a NMR spectrum at −8-−37 ppm. This corresponds to a pentacoordinate state of compounds 17 [24,[26][27][28][29][30][31]. Tetracoordinated forms of 2-fluorooxaphosphetanes 17 were not registered by 19 F-and 31 P-NMR spectroscopy (Scheme 11).…”

Section: Preparation Methodsmentioning

confidence: 99%

“…The 2-halo-1,2λ 5 -oxaphosphetanes were prepared by reaction of P-fluoro-, chloro-or bromoylides with carbonyl compounds. P-Chloro-and P-bromoylides react with active ketones, containing a trifluoromethyl group, with the formation of stable [2+2]-cycloaddition products, 2-chloro-or 2-bromo-1,2λ 5 oxaphosphetenes 14 were isolated in yields close to quantitative as crystalline substances or as liquids distillable in vacuum (Scheme 8, Table 1) [24][25][26][27][28][29][30][31][32].…”

Section: Preparation Methodsmentioning

confidence: 99%

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Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Kolodiazhna¹,

Kolodiazhnyi²

2016

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Abstract:Results of research into four-membered 2-halo-1,2λ 5 -oxaphosphetane phosphorus(V)-heterocycles are presented. The preparation of 2-halo-1,2λ 5 -oxaphosphetanes by reaction of Phaloylides with carbonyl compounds is described. The mechanism of asynchronous [2+2]-сycloaddition of ylides to aldehydes was proposed on the base of low-temperature NMR investigations. 2-Halo-1,2λ 5 -oxaphosphetanes were isolated as individual compounds and their structures were confirmed by 1 Н-, 13 C-, 19 F-and 31 Р-NMR spectra. These compounds are convenient reagents for preparing of various organic and organophosphorus compounds hardly available by other methods. Chemical and physical properties of the 2-halon-1,2λ 5 -oxaphosphetanes are reviewed. The 2-chloro-1,2λ 5 -oxaphosphetanes, rearrange with formation of 2-chloroalkylphosphonates or convert into trans-phosphorylated alkenes depending on the substituents at the α-carbon atom. Prospective synthetic applications of 2-halo-1,2λ 5 -oxaphosphetanes are analyzed. The 2-halo-1,2λ 5 -oxaphosphetanes may be easily converted to various alkenylphosphonates: allyl-or vinylphosphonates, phosphorus ketenes, thioketenes, ketenimines.

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Section: Preparation Methodsmentioning

confidence: 99%

Section: Preparation Methodsmentioning

confidence: 99%

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Kolodiazhna¹,

Kolodiazhnyi²

2016

Preprint

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“…Among the stable oxaphosphetanes [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22], 2-halo-1,2λ 5 -oxaphosphetanes 14 , which possess relatively high stability and diverse reactivity, attract particular interest [23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38] (Scheme 7). These oxaphosphetanes containing fluorine, chlorine or bromine atoms bonded to phosphorus are an interesting class of pentacoordinated phosphorus heterocycles possessing peculiar properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ5-oxaphosphetanes

Kolodiazhna

Kolodiazhnyi

2016

Molecules

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Abstract:Results of research into four-membered 2-halo-1,2λ 5 -oxaphosphetane phosphorus(V)-heterocycles are presented. The preparation of 2-halo-1,2λ 5 -oxaphosphetanes by reaction of P-haloylides with carbonyl compounds is described. The mechanism of asynchronous [2+2]-cycloaddition of ylides to aldehydes was proposed on the base of low-temperature NMR investigations. 2-Halo-1,2λ 5 -oxaphosphetanes were isolated as individual compounds and their structures were confirmed by 1 H-, 13 C-, 19 F-and 31 P-NMR spectra. These compounds are convenient reagents for preparing of various organic and organophosphorus compounds hardly available by other methods. Chemical and physical properties of the 2-halo-1,2λ 5 -oxaphosphetanes are reviewed. The 2-chloro-1,2λ 5 -oxaphosphetanes, rearrange with formation of 2-chloroalkyl-phosphonates or convert into trans-phosphorylated alkenes depending on the substituents at the α-carbon atom. Prospective synthetic applications of 2-halo-1,2λ 5 -oxaphosphetanes are analyzed. The 2-halo-1,2λ 5 -oxaphosphetanes may be easily converted to various alkenylphosphonates: allyl-or vinylphosphonates, phosphorus ketenes, thioketenes, ketenimines.

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“…in the synthesis of naturally ocurring compounds [1]. There are only a few ylides containing fluorine or perfluoroalkyl groups in the alkylidene moiety [2] and not many P-halogeno derivatives [3]. Recently, we synthesized the first P-trifluoromethyl ylides, having one CF 3 bonded to phosphorus [4].…”

Section: Introductionmentioning

confidence: 99%

P‐bis(trifluoromethyl) ylides: Synthesis and reactions

Dieckbreder

Röschenthaler

Kolomeitsev

2002

Heteroatom Chemistry

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Bis(trifluoromethyl)phosphines RP(CF3)2 (R = Me, NEt2) were methylated by MeOSO2CF3, yielding the respective phosphonium salts [RP(CF3)2Me]+ and CF3SO3−. Deprotonation using MeNP(NEt2)3 led to the phosphorus ylides RP(CF3)2CH2, stable in solution at ambient temperature, which could be converted into 1,2λ5σ5‐oxaphosphetanes by adding hexafluoroacetone. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:650–653, 2002; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10061

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Synthesis and Properties of Phosphorus Ylides Containing Fluorine Atoms Bonded to Phosphorus

Abstract: Methods for preparation of phosphorus ylides substituted at the phosphorus atom of the P=C group with fluorine atoms, their properties and application in synthesis are reviewed. The bibliography includes 77 references.

Cited by 25 publications

References 27 publications

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ5-oxaphosphetanes

P‐bis(trifluoromethyl) ylides: Synthesis and reactions

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Synthesis and Properties of Phosphorus Ylides Containing Fluorine Atoms Bonded to Phosphorus

Abstract: Methods for preparation of phosphorus ylides substituted at the phosphorus atom of the P=C group with fluorine atoms, their properties and application in synthesis are reviewed. The bibliography includes 77 references.

Cited by 25 publications

References 27 publications

Synthesis, Properties and Stereochemistry of 2-Halo-1,2&lambda;<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2&lambda;<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ5-oxaphosphetanes

P‐bis(trifluoromethyl) ylides: Synthesis and reactions

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Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes