ChemInform Abstract: REACTION OF CYCLOPENTADIENE WITH 3,3,3‐TRIFLUOROPROPYLENESULFONYL FLUORIDE

Il'in, G. F.; Kolomiets, A. F.; Sokol'skii, G. A.

doi:10.1002/chin.198152137

Cited by 3 publications

(4 citation statements)

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“…N-Hexafluoroisobutyl- [59], N-alkoxycarbonyl- [60,61], N-dialkoxyphosphoryl- [4] and N-phenylsulphonyl- [62] imines of hexafluoroacetone on interaction with HPC readily form adducts 178 (Scheme 60). Scheme -Aminophosphonate derivatives 178 (X = COOR ) were investigated as cholinesterase inhibitors [61].…”

Section: Reactions Of Haloalkaneimines With Hydrophosphoryl Compoundsmentioning

confidence: 99%

Phosphorylation of α-Haloimines: P-C vs. P-N Bond Formation

Onys’ko¹,

Rassukana²,

Sinitsa

2008

COC

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The chemoselectivity of reactions between -haloimines -compounds containing a Hal-C-C=N-skeleton -and nucleophilic phosphorus derivatives are discussed systematically. The synthetic potentialities, as well as possible mechanistic pathways of this currently developing field of organophosphorus chemistry are considered. Phosphorylation of the -haloimines leads mainly to C-or N-phosphorylated compounds as the final products, the selectivity being dependent on the type of halogen, substituents at the imine carbon and nitrogen atoms, and on the nature of phosphorus reagent. The main factors controlling regio-and stereoselectivity are elucidated. A series of novel theoretically and preparatively important transformations have also been illustrated; i.e., new diad rearrangements involving the N C and C N transfer of a sulfonyl or a phosphoryl group, the unusual acylation of the electrophilic imine carbon atom by tervalent phosphorus isocyanates, and others. Variety of transformations is connected with the possible participation of C=N bond, halogen atoms or N-substituents, in reactions involving the Hal-C-C=N-arrangement. The use of haloimines as versatile building blocks for synthesis of practically promising functionalized aminophosphonates, bisphosphonates, and phosphorus analogs of dehydro aminoacids, etc., is demonstrated.

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Section: Reactions Of Haloalkaneimines With Hydrophosphoryl Compoundsmentioning

confidence: 99%

Phosphorylation of α-Haloimines: P-C vs. P-N Bond Formation

Onys’ko¹,

Rassukana²,

Sinitsa

2008

COC

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“…In the syntheses of fluorinated α-aminoalkanephosphonates by this method the Schiff bases derived from hexafluoroacetone were examined first. These reactions proceed at room temperature without catalysts (Scheme ). ,− Imines derived from trifluoromethyl ketones and trifluoropyruvates undergo similar addition in the presence of catalytic amounts of sodium methoxide (Scheme ) . β-Fluorinated aldehydes due to their low stability are poor substrates in such reactions.…”

Section: 61 Analogues Of 1-aminoalkanephosphonic Acidsmentioning

confidence: 99%

“…These reactions proceed at room temperature without catalysts (Scheme 116). 346,[352][353][354][355] Imines derived from trifluoromethyl ketones and trifluoropyruvates undergo similar addition in the presence of catalytic amounts of sodium methoxide (Scheme 117). 356 β-Fluorinated aldehydes due to their low stability are poor substrates in such reactions.…”

Section: Analogues Of 1-aminoalkanephosphonic Acidsmentioning

confidence: 99%

Fluorinated Phosphonates: Synthesis and Biomedical Application

Romanenko¹,

Kukhar²

2006

Chem. Rev.

346

185

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“…Hexafluoroacetone iV-benzenesulfonylimine reacts with bis(tetrafluoro-propyl) phosphite to form a stable 1-aminoalkylphosphonate. 349 The kinetics and mechanism of the addition of bis(fluoroalkyl) phosphites to benzylideneacetone, chalcone, butyl cinnamate and p-methoxycinnamate, and also to a phenylglyoxylic acid ester have been investigated. 350 ' 351 The reduced reactivity of bis(fluoroalkyl) phosphites in the Abramov and Pudovik reactions as well as certain specific features of their behaviour uncharacteristic of the usual dialkyl phosphites have been noted.…”

Section: A Bis(fluoroalkyl) Phosphitesmentioning

confidence: 99%

Fluoroalkoxy-derivatives of trivalent phosphorus: synthesis and reactivity

Миронов¹,

Konovalova²,

Burnaeva³

et al. 1996

Russ. Chem. Rev.

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ContentsI. Introduction 935 II. The influence of fluorine-containing substituents on the properties of the P(III) atom. Photoelectron 935 spectroscopic and electrochemical data III. Synthesis of fluoroalkoxy-derivatives of P(III) 938 IV. Reactions of fluoroalkyl phosphites 948 V. Conclusion 966 Abstract. The review surveys and gives a systematic account of the electronic structures, syntheses, and chemical properties of fluoroalkyl derivatives of trivalent phosphorus (phosphites, thiophosphites, and amidophophites). The methods of preparation and reactivities of fluoroalkyl phosphites are compared with those of unsubstituted phosphites. The bibliography includes 420 references.

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ChemInform Abstract: REACTION OF CYCLOPENTADIENE WITH 3,3,3‐TRIFLUOROPROPYLENESULFONYL FLUORIDE

Cited by 3 publications

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Phosphorylation of α-Haloimines: P-C vs. P-N Bond Formation

Phosphorylation of α-Haloimines: P-C vs. P-N Bond Formation

Fluorinated Phosphonates: Synthesis and Biomedical Application

Fluoroalkoxy-derivatives of trivalent phosphorus: synthesis and reactivity

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ChemInform Abstract: REACTION OF CYCLOPENTADIENE WITH 3,3,3‐TRIFLUOROPROPYLENESULFONYL FLUORIDE

Cited by 3 publications

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Phosphorylation of &#945;-Haloimines: P-C vs. P-N Bond Formation

Phosphorylation of &#945;-Haloimines: P-C vs. P-N Bond Formation

Fluorinated Phosphonates: Synthesis and Biomedical Application

Fluoroalkoxy-derivatives of trivalent phosphorus: synthesis and reactivity

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Phosphorylation of α-Haloimines: P-C vs. P-N Bond Formation

Phosphorylation of α-Haloimines: P-C vs. P-N Bond Formation