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.
p-(1a), m-Nitrobenzhydroxamoyl chloride (1b), 5-nitro-2-furhydroxamoyl chloride (1c), or benzhydroxamoyl chloride (1d) was treated with acenaphthylene and indene to afford the corresponding cycloadducts (2a-d) and (3a-d) respectively. They were shown to have common isoxazoline structure on the basis of the analytical and spectral data.