Some Organic Arsenicals Containing the Arsenic-Sulfur Linkage¹

Abstract

The benzene solution was dried and concentrated. The crystalline residue was recrystallized from benzeneether and washed on the filter with ether, yield 1.28 g., m. p. 177-180°. An additional 0.17 g. was obtained from the mother liquor (total 83%). Recrystallization from the same solvent raised the m. p. to 189-190.5°, [ ]27 -46.5 =*= 3°( dioxane).

Structural characteristics of 2-halo-1,3,2-dithiarsenic compounds and tris-(pentafluorophenylthio)-arsen

“…It was previously postulated that the 2-chloro-1,3,2-dithiarsolane is first hydrolyzed at the As-Cl bond followed by breakage of the As-S bond by water, which then provides a free sulfhydryl group which can react with another equivalent of 1 to eliminate HCl [1]. However water does not seem to be the only solvent that will function successfully to break the As-S bond.…”

“…Mp: 117-119°C. 1 Mass spectra (GC-MS): 243 (As(SCH 2 ) 2 (C 6 H 4 )) + , 168 ((SCH 2 ) 2 (C 6 H 4 )) + , 104 ((CH 2 ) 2 (C 6 H 4 )) + .…”

“…The first paper on the disposal of Lewisite was published in 1946 in which a method was presented for the synthesis of 2-chloro-1,3,2-dithiarsolane [1]. The motivation for the synthesis of such compounds was the need for a safe way to dispose of Lewisite and other arsenic chlorides in the late 1940s and 1950s.…”

Synthesis and characterization of a rare arsenic trithiolate with an organic disulfide linkage and 2-chloro-benzo-1,3,2-dithiastibole

“…Arsenic thiolates have been of interest since World War II with the treatment of Lewisite poisoning (Cl 2 AsCH@ CHCl) with the dithiol 2,3-dimercaptopropanol more commonly known as British Anti-Lewisite (BAL) [1]. BAL has several undesired side effects; it causes hypertension and tachycardia as well as headache, nausea, vomiting, salivation, and pain.…”

“…The addition of 1,2-ethanedithiol to arsenic trichloride was shown to quantitatively yield 2-chloro-dithiarsolane and two equivalents of HCl [1]. The same synthetic technique was used to synthesize the compounds discussed here.…”