The preparation of diphenylchloroarsine and diphenylcyan oarsine from phenylhydrazine

Barker, Roger L.; Booth, E. T.; Jones, W. E.; Woodward, F. N.

doi:10.1002/jctb.5000680907

Cited by 16 publications

(8 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Syntheses were performed under an atmosphere of dry argon with the use of standard Schlenk techniques, although the solid complexes, once isolated, were air stable. The compounds [AuCl(tht)], [PtI 2 (1,5-COD)], and chlorodiphenylarsine were prepared by the appropriate literature procedure. All other chemicals were commercially available.…”

Section: Methodsmentioning

confidence: 99%

Divalent Platinum Complexes of the Carbanion 2-C₆F₄AsPh₂: Monodentate or Bidentate Coordination?

et al. 2013

View full text Add to dashboard Cite

The reaction of [PtI 2 (1,5-COD)] with 2-LiC 6 F 4 AsPh 2 affords the planar platinum(II) fluoroaryl complex [PtI(κC-2-C 6 F 4 AsPh 2 )(1,5-COD)] (7), in which the arsenic atom is not coordinated to the metal atom. Attempts to prepare the bis(chelate) complex [Pt(κ 2 As,C-2-C 6 F 4 AsPh 2 ) 2 ] analogous to the known phosphorus compound failed. Removal of iodide ion from 7 with TlPF 6 gave [Pt(κ 2 As,C-2-C 6 F 4 AsPh 2 )(1,5-COD)]PF 6 (8), in which 2-C 6 F 4 AsPh 2 is now coordinated as a bidentate ligand, giving a four-membered chelate ring. Alternatively, protonolysis (with triflic acid) of the methyl complex [PtMe(κC-2-C 6 F 4 AsPh 2 )(1,5-COD)] (15), which is obtained from 7 and dimethylzinc, gives the triflate salt 16 of the same chelate cation. The chelate As,C ring in 8 is readily reopened when the complex is treated with pyridine or with halide ions, forming respectively [Pt(py)(κC-2-C 6 F 4 AsPh 2 )(1,5-COD)]PF 6 (9) and [PtX(κC-2-C 6 F 4 AsPh 2 ](1,5-COD)] (X = Cl (10), Br (11), I (7)). The appearance of two pairs of olefinic COD resonances in the proton NMR spectra of 7, 10, 11, and 15 may indicate that there is restricted rotation about the Pt−κC-2-C 6 F 4 AsPh 2 bond; the additional signals are not evident in the spectra of 8 or 16. Complexes 7 and 10 form the 1:1 adducts [PtX(μ-2-C 6 F 4 AsPh 2 )(1,5-COD)AuY] (X = Cl, Y = I (12); X = Y = I (13); X = Y = Cl (14)) by attachment of gold(I) halides to their dangling arsenic atoms. In 12 the halides are scrambled between platinum and gold. The X-ray structures of 7, 8, 9, 12, 15, and 16 are reported, and possible reasons for the poorer chelating ability of 2-C 6 F 4 AsPh 2 in comparison with that of 2-C 6 H 4 PPh 2 are discussed.

show abstract

Section: Methodsmentioning

confidence: 99%

Divalent Platinum Complexes of the Carbanion 2-C₆F₄AsPh₂: Monodentate or Bidentate Coordination?

et al. 2013

View full text Add to dashboard Cite

show abstract

“…By treating the reaction mixtures with an alkali halide such as sodium chloride, the RHgCl compounds were precipitated and isolated. An interesting and unique reaction is that between phenylhydrazine and arsenic acid in the presence of hydrochloric acid to yield diphenylarsenic chloride (10).…”

Section: J Miscellaneous Methodsmentioning

confidence: 99%

Methods of Preparation of Organometallic Compounds.

Jones¹,

Gilman²

1954

Chem. Rev.

View full text Add to dashboard Cite

“…is 4.520. It was first produced in 1878 by Michaelis and La Coste by the reduction of diphenylarsonic acid with sulfur dioxide [13]. Diphenylchlorarsine is known to cause sneezing, coughing, headache, salivation, and vomiting.…”

Section: Diphenylchloroarsinementioning

confidence: 99%

Irritant Compounds: Military Respiratory Irritants. Part Ii. Sternutators

Patočka¹,

Kuča²

2016

Mil. Med. Sci. Lett.

View full text Add to dashboard Cite

Sternutators are substances that irritate the nasal and respiratory passages and cause coughing, sneezing, lacrimation, and sometimes vomiting. They are organoarsenic compounds and some of them were used as warfare toxic gases in World War I, namely diphenylaminochloroarsine, diphenylchloroarsine, diphenylcyanarsine, and phenyldichloroarsine. The effect of these irritants is in principle non-lethal.

show abstract

The preparation of diphenylchloroarsine and diphenylcyan oarsine from phenylhydrazine

Cited by 16 publications

References 1 publication

Divalent Platinum Complexes of the Carbanion 2-C₆F₄AsPh₂: Monodentate or Bidentate Coordination?

Divalent Platinum Complexes of the Carbanion 2-C₆F₄AsPh₂: Monodentate or Bidentate Coordination?

Methods of Preparation of Organometallic Compounds.

Irritant Compounds: Military Respiratory Irritants. Part Ii. Sternutators

Contact Info

Product

Resources

About

The preparation of diphenylchloroarsine and diphenylcyan oarsine from phenylhydrazine

Cited by 16 publications

References 1 publication

Divalent Platinum Complexes of the Carbanion 2-C6F4AsPh2: Monodentate or Bidentate Coordination?

Divalent Platinum Complexes of the Carbanion 2-C6F4AsPh2: Monodentate or Bidentate Coordination?

Methods of Preparation of Organometallic Compounds.

Irritant Compounds: Military Respiratory Irritants. Part Ii. Sternutators

Contact Info

Product

Resources

About

Divalent Platinum Complexes of the Carbanion 2-C₆F₄AsPh₂: Monodentate or Bidentate Coordination?

Divalent Platinum Complexes of the Carbanion 2-C₆F₄AsPh₂: Monodentate or Bidentate Coordination?