ChemInform Abstract: REACTION OF ALKYL(ARYL)DICHLOROPHOSPHINES AND N,N,N′,N′‐TETRAALKYL‐P‐PHENYLPHOSPHONOUS DIAMIDES WITH O‐AMINOPHENOL

Pudovik, M. A.; Terent'eva, S. A.; Anoshina, N. P.; Pudovik, A. N.

doi:10.1002/chin.197741327

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“…Since the PCO/POC-rearrangement in the series of derivatives of tetracoordinate phosphorus is facilitated by electron-donor substituents at the phosphorus atoms, 38,39 we performed the reaction between hexafluoroacetone and 4,5-dimethyl-2- . The ratio of the summary integral intensities of the two quartets and the two singlets is 2:1; that is, the compound 9 showing quartets in the 31 P-{ 1 H} NMR spectrum dominates in the solution.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Since the PCO/POC-rearrangement in the series of derivatives of tetracoordinate phosphorus is facilitated by electron-donor substituents at the phosphorus atoms, , we performed the reaction between hexafluoroacetone and 4,5-dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane 8 . Compound 8 contains a less electron-accepting cycle compared with the benzodioxaphosphol cycle, which still stabilizes the pentacoordinate state of phosphorus.…”

Section: Resultsmentioning

confidence: 99%

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Stereoselective PCO/POC-Rearrangement of P–C-Cage Phosphorane in the Reaction of 4,5-Dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane with Hexafluoroacetone

et al. 2016

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Interaction of 4,5-dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane, bearing a carboxyl group in the γ-position with respect to the phosphorus atom and obtained from d,l-butanediol, with hexafluoroacetone (CCl4, -40 °C) leads to the simultaneous formation of regio- and stereoisomeric cage-like phosphoranes with phosphorus-carbon and phosphorus-oxygen bonds with a high stereoselectivity (>95%), whose structure was determined by 1D and 2D NMR spectroscopy and XRD. When stored as a solution in dichloromethane for one month, the PCO-isomer rearranges into the thermodynamically more stable POC-isomer of the cage-like phosphorane. Mild hydrolysis of the PCO/POC-isomers proceeds with a high chemoselectivity and leads to the formation of P(IV)-dioxaphospholane derivatives. Acidic hydrolysis of the POC-isomer leads to the formation of an oxirane derivative with an unexpectedly high stereoselectivity (>95%). DFT calculations (using the PBE functional) allowed us to obtain structures and energies of the initial phospholane, reaction products (PCO/POC-isomers), and an intermediate P(V)-oxaphosphirane.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Stereoselective PCO/POC-Rearrangement of P–C-Cage Phosphorane in the Reaction of 4,5-Dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane with Hexafluoroacetone

et al. 2016

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ChemInform Abstract: REACTION OF ALKYL(ARYL)DICHLOROPHOSPHINES AND N,N,N′,N′‐TETRAALKYL‐P‐PHENYLPHOSPHONOUS DIAMIDES WITH O‐AMINOPHENOL

Abstract: Phenyl‐dichlorphosphit (I) und o‐Aminophenol (II) reagieren zur Spiroverbindung (III), im Reaktionsprodukt läßt sich spektroskopisch die Verbindung (IV) nachweisen.

Cited by 1 publication

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Stereoselective PCO/POC-Rearrangement of P–C-Cage Phosphorane in the Reaction of 4,5-Dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane with Hexafluoroacetone

Stereoselective PCO/POC-Rearrangement of P–C-Cage Phosphorane in the Reaction of 4,5-Dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane with Hexafluoroacetone

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