Formation of phosphorus-oxygen bonds in the reactions of triaminophosphines with o-quinones, vicinal triketones, and xoxmalonic esters.  Triaminooxyphosphonium dipolar ions and triaminodioxaphosphoranes.  Phosphorus-31 nuclear magnetic resonance spectra

Ramírez, Fausto; Patwardhan, Anand V.; Kügler, Hermann; Smith, Clark

doi:10.1021/ja01000a051

Cited by 72 publications

(35 citation statements)

References 1 publication

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“…Treatment of P(NMeCH 2 ) 2 (OMe) [10] with BH 3 AE THF yields a diaminosubstituted-phosphiteborane, BH 3 AE P(NMeCH 2 ) 2 (OMe) (1) in the analogous method [11], as a white solid in 98% yield, as shown in Eq. (1).…”

Section: Synthesis and Characterization Of Phosphiteboryl Molybdenum mentioning

confidence: 99%

Molybdenum complexes bearing a diaminosubstituted-phosphiteboryl ligand: Syntheses, structures, and reactivity involving the Mo–B, B–P, and B–H activation

Nakazawa

Itazaki

Ohba

2007

Journal of Organometallic Chemistry

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Section: Synthesis and Characterization Of Phosphiteboryl Molybdenum mentioning

confidence: 99%

Molybdenum complexes bearing a diaminosubstituted-phosphiteboryl ligand: Syntheses, structures, and reactivity involving the Mo–B, B–P, and B–H activation

Nakazawa

Itazaki

Ohba

2007

Journal of Organometallic Chemistry

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“…It is known that α-diketones react with common trialkyl phosphites to produce 1,3,2-dioxaphospholes [16]; in some cases, these compounds are unstable and are readily converted into more stable four-coordinate phosphorus compounds, the dioxaphosphole ring being conserved [17] or opened [16]. The stability of λ 5 -dioxaphosphole structure increases in going from acyclic phosphites to five-membered cyclic P(III) derivatives [18]. Dialkoxy-λ 3 -phosphanyl isocyanates having a carbonyl group in the β-position with respect to the phosphorus atom reacted with diacetyl and dibenzoyl either at both carbonyl groups to afford cycloaddition products, 1,3,2-dioxaphospholes, or at the isocyanate carbonyl group with formation of oxazaphospholanes having P-C and P-O bonds in the ring [19].…”

Section: Methodsmentioning

confidence: 99%

Reactions of 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2-benzodioxaphosphepin-5-one with phenanthrenequinone and dibenzoyl

et al. 2011

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Reactions of 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2-benzodioxaphosphepin-5-one with 9,10-phenanthrenequinone and dibenzoyl gave hydrolytically unstable spirophosphoranes with five-and seven-membered rings, 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydrospiro [[1,3,2]benzodioxaphosphepine-2,2′-phenanthro[9,10-d][1,3,2]dioxaphosphol]-5-one and 2,4′,5′-triphenyl-4,4-bis(trifluoromethyl)-4,5-dihydrospiro [[1,3,2]benzodioxaphosphepine-2,2′-[1,3,2]dioxaphosphol]-5-one. The structure of the first of these was proved by X-ray analysis. R 1 = R 2 = CF 3 ; R 1 = CCl 3 , R 2 = H. Tervalent phosphorus derivatives are key precursors of various organophosphorus compounds with different coordination numbers of the phosphorus atom [1][2][3][4]. This is related to accessibility of lone electron pair on the phosphorus atom and thermodynamic favorability for the formation of phosphoryl compounds. Cyclic phosphorylated derivatives of salicylic acid having a fairly reactive carbonyl group in the β-position with respect to the phosphorus atom occupy a specific place among P(III) compounds. They are capable of being involved in cascade reactions with activated carbonyl compounds, Schiff bases, and ylidene derivatives of dicarbonyl compounds. In these reactions, the carbonyl group can participate in one or another step of the cascade process, leading to the formation of 1,3,2-dioxa(oxaza)-and 1,4,2-dioxa-(oxaza)phosphepines, 1,2-oxaphospholanes, and other difficultly accessible compounds [5][6][7][8][9][10][11][12].We recently showed that cyclic phosphorus(III) derivatives having an activated carbonyl group in the γ-position with respect to the phosphorus atom, e.g., 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2-benzodioxaphosphepin-5-one (I), also undergo cascade transformations by the action of trichloroacetaldehyde and hexafluoroacetone. As a result, cage-like propeller phosphorane with a phosphorus-carbon bond (structure II) [13,14] or spiran structure III is formed; in the latter structure, the γ-carbonyl carbon atom becomes a spiro atom [15] (Scheme 1).

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“…(1,7,7 Trimethyl 2 oxobicyclo[2.2.1]hept 3 yloxy)tris(di ethylamino)phosphonium chloride (5). A solution of hexaethyl amidophosphite (3) (1.2 mL, 4.6 mmol), which was distilled over calcium hydride, and diethylammonium chloride (0.33 g, 3 mmol) in CH 2 Cl 2 (5 mL) was added dropwise with cooling (-20 °C) to a solution of camphoroquinone (4) (0.5 g, 3 mmol) in CH 2 Cl 2 (10 mL) under argon.…”

Section: Methodsmentioning

confidence: 99%

Reaction of 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione with hexaethyltriamidophosphite in the presence of diethylammonium chloride. Synthesis and the three-dimensional structure of (1,7,7-trimethyl-2-oxobicyclo[2.2.1]hept-3-yloxy)tris(diethylamino)phosphonium chloride

et al. 2006

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Reaction of 1,7,7 trimethylbicyclo[2.2.1]heptane 2,3 dione with hexaethyltriamidophosphite in the presence of diethylammonium chloride.Synthesis and the three dimensional structure of (1,7,7 trimethyl 2 oxobicyclo[2. 2.1]hept 3 yloxy)tris(diethylamino)phosphonium chlorideThe reaction of 1,7,7 trimethylbicyclo[2.2.1]heptane 2,3 dione with hexaethyltriamido phosphite in the presence of diethylammonium chloride afforded a stable quasiphosphonium salt, viz., (1,7,7 trimethyl 2 oxobicyclo[2.2.1]hept 3 yloxy)tris(diethylamino)phosphonium chloride, as one diastereomer (racemate, 1R*,3S*,4S*).

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Formation of phosphorus-oxygen bonds in the reactions of triaminophosphines with o-quinones, vicinal triketones, and xoxmalonic esters. Triaminooxyphosphonium dipolar ions and triaminodioxaphosphoranes. Phosphorus-31 nuclear magnetic resonance spectra

Cited by 72 publications

References 1 publication

Molybdenum complexes bearing a diaminosubstituted-phosphiteboryl ligand: Syntheses, structures, and reactivity involving the Mo–B, B–P, and B–H activation

Molybdenum complexes bearing a diaminosubstituted-phosphiteboryl ligand: Syntheses, structures, and reactivity involving the Mo–B, B–P, and B–H activation

Reactions of 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2-benzodioxaphosphepin-5-one with phenanthrenequinone and dibenzoyl

Reaction of 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione with hexaethyltriamidophosphite in the presence of diethylammonium chloride. Synthesis and the three-dimensional structure of (1,7,7-trimethyl-2-oxobicyclo[2.2.1]hept-3-yloxy)tris(diethylamino)phosphonium chloride

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