E. A. Rowe, Louis Reisman, Jennifer A. Jefcoat
Oct 16, 2019
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0
Influential Citations
10
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Journal
Macromolecules
Abstract
N-sulfonylazetidines undergo anionic ring-opening polymerization (AROP) to form poly(N-sulfonylazetidine)s, which are potential precursors to valuable polyimines. In this work, the impacts of alkyl sulfonyl substitution on the AROP of (N-(ethanesulfonyl)azetidine (EsAzet), N-(2-propanesulfonyl)azetidine (iPsAzet), and N-(tert-butylsulfonyl)azetidine (tBsAzet) are studied and compared to those of the previously reported polymerization of N-(methanesulfonyl)azetidine (MsAzet). The polymerization kinetics of EsAzet and iPsAzet is of the first order with respect to their monomers and produces p(EsAzet) and p(iPsAzet), which are both soluble in DMF and DMSO. In contrast, the polymerization of tBsAzet proceeds only to low conversion due to precipitation of p(tBsAzet) under identical conditions. At lower temperatures (120 °C), iPsAzet polymerizes with the fastest rate, while at higher temperatures (180 °C), the rate of MsAzet is the fastest. The reordering of the relative polymerization rates of MsAzet, EsAzet, ...