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Published September 1981 | public
Journal Article

Backbone-assisted reactions of polymers. 2. Poly[(chloromethyl)thiirane]

Abstract

The conversion of (chloromethy1)thiirane to poly[(chloromethyl)thiirane] of molecular weight ca. 20 000 was accomplished by using boron trifluoride etherate as initiator. Initiators based on cadmium, zinc, or aluminum were less effective, and the anionic initiators KOH and NaNH2 produced no polymer. Poly[(chloromethyl)thiirane] was found to undergo an unusual structural rearrangement at room temperature in the absence of solvent and to hydrolyze in a dioxane/water mixture at a rate much greater than that observed for poly(epichlorohydrin). These results suggest important anchimeric assistance by the backbone sulfur atom in the reactions of poly[ (chloromethyl)thiirane].

Additional Information

© 1981 american Chemical Society. Received March 11, 1981. We are grateful to Dr. Joanne Smith (Coatings and Resins Research Center, PPG Industries, Inc.) for providing ¹³C NMR spectra and to Ms. Barbara A. Meindl for polymer hydrolysis experiments. This work was supported by the Dow Chemical Grant of the Research Corp. and by the National Science Foundation (Polymers Program, Grant DMR 8001629). Support of our research by Lord Corp. is also gratefully acknowledged.

Additional details

Created:
August 19, 2023
Modified:
October 19, 2023