有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
p-ビニルベンジルエーテルおよびP-ビニルベンジルスルフィドの合成と重合
谷本 重夫西 政治岡野 正弥小田 良平
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1969 年 27 巻 9 号 p. 858-862

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p- (β-Bromoethyl) benzyl chloride was treated with sodium alcoholate at room temperature to obtain p-vinylbenzyl ether, which could be polymerized in bulk using 2, 2'-azobisisobutyronitrile as an initiator.
BrCH2 CH2-_??_-CH2 CINaOR→CH2=CH-_??_CH2 OR→ [-CH-CH2-_??_-CH2OR] n R=C2H5, CH3, (CH2) 2CH3, CH (CH3) 2, CH2CH=CH2, (CH2) 3CH3, CH2CH (CH3) 2
Sodium tert-butyrate failed to give the expected tert-butyl ether. Instead, p-chloromethylstyrene was the only product isolated.
Using sodium mercaptide under analogous conditions, p-vinylbenzyl sulfide was synthesized, from which a new polymer was obtained as follows ;
BrCH2CH2-_??_-CH2ClNasR→BrCH2CH2-_??_-CH2SRKOH→CH2=CH-_??_-CH2SR→ [-CH-CH2-_??_-CH2SR] n R=C2H5, (CH2) 2CH3

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