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Synthetic Applications of Flexible SNO-OCT Strained Alkynes and Their Use in Postpolymerization Modifications
Eileen G Burke1, Jennifer M Schomaker1
1Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
Abstract:
SNO-OCTs are eight-membered heterocyclic alkynes that have fast rates of reactivity with 1,3-dipoles. In contrast to many other reported cycloalkynes, SNO-OCTs contain multiple sites for derivatization, display stability under a variety of common reaction conditions, and offer the opportunity for strain-induced ring-opening following the initial reaction of the alkyne moiety. In this paper, we describe how the unique features of SNO-OCTs can be employed to modify an oxime-bearing styrene copolymer and introduce an array of polar functionalities into the polymer. This can be achieved through both the addition of SNO-OCT to the polymer, as well as in the subsequent opening of the sulfamate ring once it has been installed in the polymer.
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