β-クロルビニルスルホンの合成と反応

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β-Chlorovinyl ketones are known to be very reactive toward nucleophilic substilutione In the present study, β-chlorovinyl sulfones were synthesized and their reactions investigated. Thus, condensation of arylsulfonyl chloride with vinyl chloride followed by dehydrochlorination with the aid of triethylamine gave the following; β-chlorovinyl-p-tolyl sulfone (3a) (mp 4347°C), β-chlorovinyl-2, 4-dimethylphenyl sulfone (3b) (bp 135142°C/0.12 mmHg), β-chlorovinyl-2, 5-dimethylphenyl sulfone (3c) (mp 99.5102.5°C), and 4, 4-bis- (β-chlorovinylsulfonyl) -phenoxybenzene (3d) (mp 127132°C). All those β-chlorovinyl sulfones were trans-isomers. The reactions of (3a) with Bisphenol-A or cyclohexylamine, (3b) with methanol, and (3d) with diethylamine were studied. (3d) was also condensed with hexamethylenediamine, ethylenediamine, and Bisphenol-A to obtain polymers with intrinsic viscosities of 0.20 dl.g-1 (dimethylformamide, 30°C), 0.16 dl.g-1 (dimethylformamide, 30°C), and 0.09 dl.g-1 (dioxan, 30°C), respectively.
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