Sulfanion-initiated open-vessel anionic ring-opening polymerization (AROP) of N-sulfonyl aziridines

Telechelic block copolymer L-PPI-b-poly(epoxide-alt-PA) obtained via desulfonation of poly(o-nitrophenylsulfonyl-activated aziridines)

“…28,29 Different activating N-sulfonyl groups have been investigated for the anionic ring-opening polymerization (AROP) of N-sulfonylaziridines. [30][31][32][33][34] The reactivity of N-sulfonylaziridines depends on the proper strength of the electron-withdrawing effect of N-sulfonyl groups and the presence of substituents. 35 The specific N-sulfonylaziridine namely N-((o-nitrophenyl)sulfonyl)aziridine (oNsAz) reported by Rupar's group could undergo ring-opening polymerization by residual hydroxide ions because of the absence of substituents and strong electron-withdrawing o-nitrophenylsulfonyl groups.…”

Green synthesis of well-defined linear poly(hydroxyl thioether) direct from epoxide in water

“…Moreover, the sulfanion-initiated AROP of N -sulfonyl aziridine in an open vessel has been demonstrated to offer polyaziridine with low to moderate MW, owing to good stability and tolerance of living sulfanion to air and limited amount of water. 21 Nevertheless, polyether or polyaziridine containing well-defined hydroxyl groups was usually produced by AROP of epoxide or aziridine with protected hydroxyl group and subsequent acidic hydrolysis. 17 Only the azaanion-initiated AROP of 2- ω -propanol- N -tosylaziridine could directly afford a hydroxyl-containing polyaziridine with very low MW, and also a small amount of branched structure cannot be ruled out.…”