Thionylchlorid als bequemer Ersatz für Phosphorpentachlorid im Gebiet der Imidchloride

Braun, Julius v.; Pinkernelle, Walter

doi:10.1002/cber.19340670719

Cited by 44 publications

(29 citation statements)

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“…N-(p-Anisyl)benzenecarboxyimidoyl chloride (1b): Synthesized by a procedure similar to [67] by stirring of a mixture of N-(p-anisyl)benzamide (3.964 g, 17.44 mmol) with thionyl chloride (2.5 mL, 34.27 mmol) at 80 8C for 2.5 h. Excess SOCl 2 was removed under reduced pressure, and the residue was distilled under vacuum affording 1b as pale yellow crystals; yield: 3.641 g (85%); bp 174-176 8C (2 Torr). N-(p-Anisyl)-2,2,2-trifluoroethanimidoyl chloride (1h): Synthesized by the method described in the literature.…”

Section: Methodsmentioning

confidence: 99%

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Catalytic Hydrogenation of α‐Iminophosphonates as a Method for the Synthesis of Racemic and Optically Active α‐Aminophosphonates

et al. 2008

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Section: Methodsmentioning

confidence: 99%

“…N-Phenylbenzenecarboxyimidoyl chloride (1a) was synthesized as published. [67] The melting points of products were measured with Electrothermal 9100 indicator in a sealed capillary.…”

Section: Methodsmentioning

confidence: 99%

Catalytic Hydrogenation of α‐Iminophosphonates as a Method for the Synthesis of Racemic and Optically Active α‐Aminophosphonates

et al. 2008

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“…Imidoyl chlorides IIIa and IIIb [19,20] were prepared by the reaction of the corresponding amides PhCONHCHRR`with thionyl chloride. Compounds IIId [6] and IIIe [21] were prepared according to published procedures.…”

Section: Methodsmentioning

confidence: 99%

“…The 1 H, 19 F, 31 P, and 13 C NMR spectra were measured on a Varian VXR-300 NMR spectrometer, working frequences 299.95, 282.20, 121.42, and 75.429 MHz, respectively. The chemical shifts were measured against internal TMS ( 1 H, 13 C), CFCl 3 ( 19 F), and external 85% phosphoric acid ( 31 P).…”

Section: Methodsmentioning

confidence: 99%

Sigmatropic isomerizations in azaallyl systems: XX. N-Alkylbenzimidoylphosphonates

et al. 2004

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Synthetic approaches are developed to benzimidoylphosphoryl derivatives containing electronically and sterically diverse alkyl substituents on the nitrogen atom, as well as their prototropic isomers. Regularities in prototropic transitions in the phosphorylated C=N!C triad were revealed and applied in the synthesis of =-aminophosphonic acid derivatives.Imidoylphosphonates containing a-hydrogen atoms in the N-alkyl group are potential 1,3-prototropic systems. Prototropy the phosphorylated C=N3C 1,3-prototropic triad presents both theoretical and practical interest. The A 76 47 B interconversion can be regarded as a [phosphorus] model of the biochemical transamination reaction in living bodies.The 1,3-prototropic shift in the phosphorylated azaallyl triad makes evident genetic relation between derivatives of imidoylphosphonic (A) and a-aminoalkylphosphonic acids (B) that attract increased interest in view of their biological activity [2, 3].Transformations like A 6 B belong to fundamental properties of imidoylphosphonates and form an important method for preparing a-aminoalkylphosphoryl derivatives [4].In previous communications of this series we showed that the phosphorus-containing group controls facility and direction of prototropic migrations in the C=N3C triad. In detail it was established [4,5] that N-benzylbenzimidoylphosphoryl derivatives I under mild conditions, even in the absence of bases, undergo an irreversible 1,3-prototropic shift to form Nbenzylidene-a-aminoalkylphosphoryl derivatives II (Scheme 1).To assess the effect of the N-alkyl substituent on the prototropy in the C3N3C triad, in the present work ÄÄÄÄÄÄÄÄÄÄÄÄ 1 For communication XIX, see [1]. Scheme 1.; C 9 0 P ; 9 0 P = T

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“…These chlorides were most conveniently prepared from the benzoylaniline, using a small excess of thionyl chloride (8,9). The use of phosphorus pentachloride (10, 11) resulted in considerable polymerization on distilling the chloride.…”

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Preparation of diphenylamines via the Chapman rearrangement

Wheeler¹,

Roman²,

Santiago³

et al. 1969

Can. J. Chem.

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Thionylchlorid als bequemer Ersatz für Phosphorpentachlorid im Gebiet der Imidchloride

Abstract: v. Bra u n , P i n k e r n e 11 e : Thionylchlorid [Jahrg. 67 J u l i u s v. B r a u n und W a l t e r P i n k e r n e l l e : Thionylchlorid als bequemer Ersatz fur Phosphorpentachlorid im Gebiet der Imidchloride.[ A m d. Chem. Institut d. Urliversitat Frankfurt a. M.]

Cited by 44 publications

References 4 publications

Catalytic Hydrogenation of α‐Iminophosphonates as a Method for the Synthesis of Racemic and Optically Active α‐Aminophosphonates

Catalytic Hydrogenation of α‐Iminophosphonates as a Method for the Synthesis of Racemic and Optically Active α‐Aminophosphonates

Sigmatropic isomerizations in azaallyl systems: XX. N-Alkylbenzimidoylphosphonates

Preparation of diphenylamines via the Chapman rearrangement

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