CCXXXVI.—Decomposition of some halogenated sulphides, and the nature of the “polymeric” ethylene sulphides

The Preparation of Nitriles.

“…Similar behavior is exhibited by amidoalkyl chlorides (72) and aminoalkyl chlorides (121). An unexpected byproduct was observed in the case of the reaction of bis(/3-chloroethyl) sulfide (mustard gas) and potassium cyanide (43). If the halogen is attached to a carbon atom bound to an oxygen atom, as in -chloroalkyl esters (85) or ethers, a pronounced activation is noted.…”

The reaction of nucleic acids with mustard gas

“…First, it is possible that half of the reacting H molecules have cross-linked non-titratable groups and the other halfentered into cross linkages with titratable groups; such circumstances, although in agreement with the analytical results, are considered not only to be statistically improbable but also unlikely to occur at pH 7. Secondly, there is the possibility that the reactions with H are more complex in character and resemble *the formation and decomposition of sulphonium salts known to occur between H and its substituted derivatives (Bell, Bennett & Hock, 1927). This reaction mechanism is considered to be most improbable since the formation of sulphonium salts is exceedingly slow at room temperature, and also since no 'sulphonium' dissociation was detected by electrometric titration.…”

Degradation of Sulfur Mustard on Moist Sand as Determined by13C Solid‐State Magic Angle Spinning Nuclear Magnetic Resonance

“…[31] Wagner et al [32] studied the thermal degradation of sulfur mustard with and without water, finding that the "dry degradation" products were 1,2-dichloroethane, polysulfides, Q (ClCH 2 CH 2 SCH 2 CH 2 SCH 2-CH 2 Cl), and 1,4-dithiane, whereas the "moist degradation" products were 1,4-oxathiane, 2-chloroethanol, and numerous sulfonium ions. The product 1,4-dithiane from the thermal decomposition of mustard was observed by Williams, [33] and its presence was explained by Bell et al [34] via a mechanism that involved sulfonium ion intermediates.…”