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The only substance isolated is polymeric 2-chlorovinylarsinoxide, a white insoluble powder.

The cold aqueous media of pH = 0.5 Lewisite decomposes as follows (5-21):

The vesicant character of arsenicals such as Lewisite is not a property of the AsCl2 group exclusively, since carefully prepared solutions of corresponding oxide or dihydroxide are equally vesicant. Lewisite reacts with sodium alkoxides to give derivatives that are volatile, vesicant liquids (5-22) that hydrolyze irreversibly on contact with water:

Reaction with sodium mercaptides gives the analogous thioethers (5-23), which are only slightly soluble in water and in general are hydrolyzed reversibly, giving toxic and sometimes vesicant solutions, although the equilibrium generally favors thioether formation (5-24):

Aqueous and alcoholic solutions of sodium dialkyldithiocarbamates react readily with Lewisite to give crystalline, sharp-melting solids that are useful for its characterization (5-25). These dithiocarbamates are much more stable than the simple thioethers. However, hydrolysis of cyclic thioethers, such as the reaction product of Lewisite and BAL (British Anti-Lewisite) (5-26) is negligible.

Alkali hydrolyzes all of these compounds with the evolution of acetylene (5-21). Hydrogen peroxide causes decomposition of the ethers and thioethers in neutral or acid solution, giving free arsenic acids.

Little information is available in the literature concerning the reactions of Lewisite with biologically important molecules, although it is reasonable to assume that, as with sulfur mustard, DNA is a major target.



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