高分子S-イリドの生成と応用

概要

論文の詳細を見る
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.
社団法人有機合成化学協会の論文