Reaction of Chloroalkyl Sulfides with Sodium

Cleavage of the Carbon-Sulfur Bond in Divalent Sulfur Compounds.

“…This is in agreement with the idea of cleavage via an intermediate sulfonium compound, i.e., the secondary carbon-sulfur bonds are cleaved in preference to primary carbon-sulfur bonds. Similar ethyleneimmonium intermediates from ß-substituted ethylamines have recently been demonstrated by kinetic and preparative methods, in connection with studies on nitrogen mustards (e.g., 27, 176 greater ease of cleavage of a tertiary carbon-sulfur bond is shown by the following reaction (219):…”

“…With 2-chloroethyl sulfides (RSCH2CH2C1) the main reaction is cleavage, with formation of ethylene (219). The evolution of ethylene is more rapid when R is tertiary butyl than it is when R is a primary or secondary group; zinc is also effective in the reaction (219).…”

“…With 2-chloroethyl sulfides (RSCH2CH2C1) the main reaction is cleavage, with formation of ethylene (219). The evolution of ethylene is more rapid when R is tertiary butyl than it is when R is a primary or secondary group; zinc is also effective in the reaction (219). Magnesium metal does not react with C1CH2-CIRSCeHs (5, 219), but the bromo compound, BrCH2CH2SCeH6, is rapidly attacked according to the above equation ( 5).…”

“…+ RSNa + NaCl + toluene y CH2 RSCH2CH2CH2SR (IV-9) The -chlorobutyl compounds yield n-butane, ethylene, 1-butene, and RS(CH2)4SR as well as some cyclic sulfonium compound (219).…”

Polymers and Sulfur: what are Organic Polysulfides Good For? Preparative Strategies and Biological Applications

“…It is worth mentioning that, in contrast to the “monomer route” (i.e., the use of sulfone‐containing monomers), at the beginning of the '70s a “polymer route” to polysulfones was proposed (Figure 3), which allowed to convert preformed aromatic polysulfides into the corresponding polysulfones by the help of hydrogen peroxide 59. Literature offers a number of later examples of this approach, which has been applied to the oxidation of aliphatic [such as poly(thietane),75 poly(ethylene sulfide)153, 154 and poly(hexene sulfide)155] and aromatic55, 57, 156 polysulfides to polysulfones. It is noteworthy that the “polymer route” may be the only way to produce main‐chain aliphatic polysulfones with the narrow MW dispersion typical of “living” chain polymerisation mechanisms, since the synthesis of sulfone‐contained strained rings (analogous to episulfides) is generally non‐trivial 157…”