Syntheses ofp-Vinylbenzyl Ethers and p-Vinylbenzyl Sulfides and Their Polymerizations

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) 2Sodium 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