Synthesis of a Δ<sup>4</sup>‐1,4,2λ<sup>5</sup>‐Selenazaphospholine, the First Selenophosphorane

Burger, Klaus; Ottlinger, R.; Frank, Albin; Schubert, Ulrich

doi:10.1002/anie.197807741

Cited by 8 publications

References 4 publications

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Fünfgliedrige Chalkogen‐Heterocyclen als Synthone für Heterodiene Synthese von Δ⁴‐1,4,2λ⁵‐Thiaza‐ und Δ⁴‐1,4,2λ⁵‐Selenazaphospholinen

et al. 1980

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Five-Membered Chalcogen Heterocycles as Synthons for HeterodienesSynthesis of A4-1,4,2hs-Thiaza-and A4-l,4,2h5-Selena~aphospholines1) Syntheses of 3,3-bis(trifluoromethyl)-3H-1,2,4-thiaselenazoles 3, -3H-1,2,4-thiatellurazoles 4, and -3H-1,2,4-diselenazoles 13 are described. These new classes of compounds can be used as synthons for 1-thia-3-aza-1,3-butadienes and 1 -selena-3-aza-l,3-butadienes. This strategy offers simple new synthetic routes to numerous heterocyclic systems like A4-1,4,2h5-thiazaphospholines 9, A4-l ,4,2h5-selenazaphospholines 15, Az-1,3-thiazolines 11, A2-1 ,3-selenazolines 16, 4H-1,3-thiazines 12, and 4H-1,3-selenazines 17. 2,2-Bis(trifluormethy1)-

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Fünfgliedrige Chalkogen‐Heterocyclen als Synthone für Heterodiene Synthese von Δ⁴‐1,4,2λ⁵‐Thiaza‐ und Δ⁴‐1,4,2λ⁵‐Selenazaphospholinen

et al. 1980

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Synthesis and Characterization of 2‐Arylseleno‐2‐chloro‐1,2,3‐triorgano‐1,3,2λ⁵‐diazaphosphetidin‐4‐ones

Pinchuk

Müller

Thönnessen

et al. 1996

Zeitschrift anorg allge chemie

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The reactions of N,N′‐dimethyl‐N,N′‐bis(trimethylsilyl)urea 8 and N‐methyl‐N′‐phenyl‐N,N′‐bis(trimethylsilyl)urea 9 with phenylselenenyl chloride 6 and p‐chlorophenylselenenyl chloride 7 furnished the N‐arylseleno‐N,N′‐diorgano‐N′‐(trimethylsilyl)ureas 10–13. The reactions of 10–13 with MePCl2 and PhPCl2 resulted in the formation of a new class of compounds, the 2‐arylseleno‐2‐chloro‐1,2,3‐triorgano‐1,3,2λ5‐diazaphosphetidin‐4‐ones 14–19. The new selenophosphoranes 20 and 21 were obtained in the reaction of 15 and 17 with p‐nitrophenol in the presence of triethylamine. The identity and structure of the new compounds were established by 1H‐ and 13C‐NMR spectroscopy, elemental analysis, 31P‐ and 77Se‐NMR spectroscopy in the case of the selenophosphoranes 14–21, and mass spectrometry in the case of 11 and 13. A possible mechanism of the reaction leading to the selenophosphoranes is discussed. Single‐crystal X‐ray structure analyses of the selenophosphoranes 19 and 20 were conducted. Both display distorted trigonal bipyramidal geometry at phosphorus, the major distortions being imposed by the four‐membered rings.

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Non-biological aspects of phosphorus-31 NMR spectroscopy

Gorenstein

1984

Progress in Nuclear Magnetic Resonance Spectroscopy

103

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Synthesis of a Δ⁴‐1,4,2λ⁵‐Selenazaphospholine, the First Selenophosphorane

Abstract: A phosphorus atom with three oxygen, one carbon, and one selenium ligand is to be found in the spiro compound (3). This species is the first representative of the selenophosphoranes proposed on several occasions as intermediates.

Cited by 8 publications

References 4 publications

Fünfgliedrige Chalkogen‐Heterocyclen als Synthone für Heterodiene Synthese von Δ⁴‐1,4,2λ⁵‐Thiaza‐ und Δ⁴‐1,4,2λ⁵‐Selenazaphospholinen

Fünfgliedrige Chalkogen‐Heterocyclen als Synthone für Heterodiene Synthese von Δ⁴‐1,4,2λ⁵‐Thiaza‐ und Δ⁴‐1,4,2λ⁵‐Selenazaphospholinen

Synthesis and Characterization of 2‐Arylseleno‐2‐chloro‐1,2,3‐triorgano‐1,3,2λ⁵‐diazaphosphetidin‐4‐ones

Non-biological aspects of phosphorus-31 NMR spectroscopy

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Synthesis of a Δ4‐1,4,2λ5‐Selenazaphospholine, the First Selenophosphorane

Abstract: A phosphorus atom with three oxygen, one carbon, and one selenium ligand is to be found in the spiro compound (3). This species is the first representative of the selenophosphoranes proposed on several occasions as intermediates.

Cited by 8 publications

References 4 publications

Fünfgliedrige Chalkogen‐Heterocyclen als Synthone für Heterodiene Synthese von Δ4‐1,4,2λ5‐Thiaza‐ und Δ4‐1,4,2λ5‐Selenazaphospholinen

Fünfgliedrige Chalkogen‐Heterocyclen als Synthone für Heterodiene Synthese von Δ4‐1,4,2λ5‐Thiaza‐ und Δ4‐1,4,2λ5‐Selenazaphospholinen

Synthesis and Characterization of 2‐Arylseleno‐2‐chloro‐1,2,3‐triorgano‐1,3,2λ5‐diazaphosphetidin‐4‐ones

Non-biological aspects of phosphorus-31 NMR spectroscopy

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Synthesis of a Δ⁴‐1,4,2λ⁵‐Selenazaphospholine, the First Selenophosphorane

Fünfgliedrige Chalkogen‐Heterocyclen als Synthone für Heterodiene Synthese von Δ⁴‐1,4,2λ⁵‐Thiaza‐ und Δ⁴‐1,4,2λ⁵‐Selenazaphospholinen

Fünfgliedrige Chalkogen‐Heterocyclen als Synthone für Heterodiene Synthese von Δ⁴‐1,4,2λ⁵‐Thiaza‐ und Δ⁴‐1,4,2λ⁵‐Selenazaphospholinen

Synthesis and Characterization of 2‐Arylseleno‐2‐chloro‐1,2,3‐triorgano‐1,3,2λ⁵‐diazaphosphetidin‐4‐ones