p-Vinylphenyl methyl sulfide prepared by the reduction of
p- (methylmercapto) acetophenone using lithium aluminium hydride with subsequent dehydration with the aid of potassium hydrogen sulfate could be bulk-polymerized in the presence of an initiator, 2, 2'-azobisisobutyronitrile. The linear sulfide-type polymer so formed was treated with dimethyl sulfate to obtain a water-soluble sulfonium-type derivative. A water insoluble sulfonium-type polymer was prepared in a similar manner from a
p-vinylphenyl methyl sulfide-divinylbenzene copolymer.
The sulfonium-type polymers were readily converted into polymer
S-ylides in dry dimethyl sulf oxide containing potassium
tirt-butoxide. The ylide reacted as a nucleophile with benzaldehyde to give styrene oxide.
A cross-linked sulfoxide-type polymer, a polystyrene derivative, containing pendant sulf oxide groups was prepared by the oxidation of
p-vinylbenzyl methyl sulfide-divinylbenzene copolymer with hydrogen peroxide.
An analogous polymer
S-ylide could also be prepared from sodium hydride and an oxosulfonium-type polymer, which had been prepared from a sulfoxide-type polymer and methyl iodide. It was noted that styrene oxide could also be obtained from such a polymer
S-ylide and benzaldehyde.
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