Forgotten monomers: access to α‐modified N‐vinylpyrrolidone polymers via C‐alkylation

Abstract Alkylation of N ‐vinylpyrrolidone using lithium diisopropylamide and bis(2‐bromoethyl) ether was carried out to obtain 3‐(2‐(2‐bromoethoxy)ethyl)‐1‐vinyl‐2‐pyrrolidone ( 2 ). The derivative 2 represents a versatile starting molecule for further modification via nucleophilic displacement yielding, for example, the bicyclic 2‐vinyl‐8‐oxa‐2‐azaspiro[4.5]decan‐1‐one ( 4 ) or the ammonium salt 3‐diethoxy‐ N , N ′‐((dimethylbenzyl)ammonium bromide)‐1‐vinyl‐2‐pyrrolidone ( 10 ). Via free radical polymerization of 4 and 10 , the corresponding homopolymers were obtained. Copolymerization of 4 and 10 with N , N ′‐diethylacrylamide yielded water‐soluble materials. The thermosensitive solubility of copolymers poly[(2‐vinyl‐8‐oxa‐2‐azaspiro[4.5]decan‐1‐one)‐ co ‐( N , N ′‐diethylacrylamide)] and poly[(3‐diethoxy‐ N , N ′‐((dimethylbenzyl)ammonium bromide)‐1‐vinyl‐2‐pyrrolidone)‐ co ‐( N ‐vinylpyrrolidone)] in water was investigated. © 2015 Society of Chemical Industry