Addition reactions of compounds with the P(:O)H group to fluorinated ketimines

Neda, Ion; Pinchuk, Vasily A.; Fischer, Axel; Jones, Peter G.; Schmutzler, Reinhard; Shermolovich, Yuri G.

doi:10.1016/0022-1139(94)03092-e

Cited by 12 publications

(4 citation statements)

References 12 publications

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“…The first reported addition of a phosphine oxide to a C=N bond was performed in 1995 by Schmutzler. [34] The reaction was performed between a variety of phosphine oxides and aryltrifluoromethylketimines (Scheme 15). It was found that in most cases a catalytic amount of NEt 3 was required for the reaction to proceed, with a notable exception being the addition of 1,3,5-triaza-4,6-dione phosphine oxide.…”

Section: Phosphine Oxidesmentioning

confidence: 99%

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Hydrophosphorylation of C=O/N Bonds Using Organophosphine Oxides or Sulfides

Lamberink‐Ilupeju,

Ragogna,

Blacquiere

2023

Eur J Inorg Chem

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Abstractα‐Functionalized phosphorus compounds are an important class of biologically relevant molecules. The synthesis of these compounds often proceeds through the hydrophosphorylation of a C=E bond, with the most well‐known transformation being the Kabachnik‐Fields reaction. The nature of the phosphorus reagent is an important aspect of the hydrophosphorylation reaction. The Kabachnik‐Fields reaction uses H‐phosphonates (RO)2P(O)H, and similarities are often applied to 2° phosphine chalcogenides (R2P(Ch)H). However, the reactivities of the P−C and P−OR molecules differ quite dramatically, which changes the operative mechanism as well as subsequent downstream chemistry. We provide an in‐depth analysis of hydrophosphorylation of C=E (E=O, N) bonds with organophosphine chalcogenides. Additional discussion and a critical appraisal are provided on the similarities and differences between the H‐phosphonate and phosphine chalcogenide chemistry.

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Section: Phosphine Oxidesmentioning

confidence: 99%

“…The first reported addition of a phosphine oxide to a C=N bond was performed in 1995 by Schmutzler [34] . The reaction was performed between a variety of phosphine oxides and aryltrifluoromethylketimines (Scheme 15).…”

Section: Addition Of Phosphine Chalcogenides To C=n Bondsmentioning

confidence: 99%

Hydrophosphorylation of C=O/N Bonds Using Organophosphine Oxides or Sulfides

Lamberink‐Ilupeju,

Ragogna,

Blacquiere

2023

Eur J Inorg Chem

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“…Ansatz: 1.41 g (4.16 mmol) 2 in 15 ml Dichlormethan; 0.49 g (4.18, mmol) Dimethylaminotrimethylsilan. : 6 = 2.28 (d,6 H (CH,),]'; 77 (8) [C,H,]'. C,,H,,CIN,OP (347.78) Ber.…”

Section: Darstellung Von 56-benzo-2-(nn-dimethylamino)-l -Methyl-3-unclassified

Darstellung Und Charakterisierung Von 2-Amino- Und 2-Methoxysubstituierten Benzodiazaphosphorinonen Mit Phosphor in Den Koordinationszahlen Drei, Vier Und Fünf

Melnicky

Neda

Schmutzler

1995

Phosphorus, Sulfur, and Silicon and the Related Elements

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This communication describes the preparation of methoxy (4-6) and dimethylamino (7-9) derivatives of the reactive chlorodiazaphosphorinone heterocycles, 1-3, using trimethylsilylmethylether and trimethyldimethylaminosilane, respectively, as reagents. The methoxy compounds 4 and 5 were converted into the P(:O)CI-derivatives 10 and 11 by reaction with sulfuryl chloride. The PNH(CH,CH,CI) derivative 12 was obtained in the reaction of the phosphoryl chloride 11 with 2-chloroethylamine hydrochloride/triethylatnine. The P(II1) derivative 7 and the previously known compound 14 were oxidized to the phosphoryl (A'P) species 13 and 15, using the urea/hydrogen peroxide 1:l adduct. Finally, the oxidative addition of two molecules of hexafluoroacetone to 9, with formation of the perfluoropinacolyl spirophosphorane 16 is described. The characterization of the new compounds rests on their n.m.r. (IH-. "C-, "F-, and "P-) spectral, and mass spectrometric data, in addition to elemental analyses.

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“…phonic acids and their derivatives [7][8][9][10][11][12][13][14][15][16][17], whereas much less is known about the corresponding ␣-aminophosphine oxides [18][19][20]. In the course of our studies of the addition of dimethylphosphine oxide to C‫ס‬O and C‫ס‬N double bonds [20][21][22][23] and of the synthesis of 4-thiazolidinylphosphonates and derivatives [24][25][26], we now wish to describe the syntheses of several new 3-thiazolines and their dimethylphosphine oxide adducts. Such ␣-aminophosphine oxides may be interesting substitutes for proline and other cyclic amino acids in the C-terminal position of peptides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of dimethyl 4-thiazolidinylphosphine oxides via addition of dimethylphosphine oxide to 3-thiazolines

et al. 1997

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The addition of dimethylphosphine oxide and its trimethylsiloxyphosphorus(III) derivative, generated in situ, to 3‐thiazolines was found to yield dimethyl 4‐thiazolidinylphosphine oxides via three different synthetic routes. The structures of two products were confirmed by X‐ray analysis; common features include approximate envelope conformations of the five‐membered rings and hydrogen bonding of the form N–H· · ·O=P. © 1997 John Wiley & Sons, Inc. Heteroatom Chem 8: 207–215, 1997.

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Addition reactions of compounds with the P(:O)H group to fluorinated ketimines

Cited by 12 publications

References 12 publications

Hydrophosphorylation of C=O/N Bonds Using Organophosphine Oxides or Sulfides

Hydrophosphorylation of C=O/N Bonds Using Organophosphine Oxides or Sulfides

Darstellung Und Charakterisierung Von 2-Amino- Und 2-Methoxysubstituierten Benzodiazaphosphorinonen Mit Phosphor in Den Koordinationszahlen Drei, Vier Und Fünf

Synthesis of dimethyl 4-thiazolidinylphosphine oxides via addition of dimethylphosphine oxide to 3-thiazolines

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