Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Synthetic Applications of Flexible SNO-OCT Strained Alkynes and Their Use in Postpolymerization Modifications

Synthetic Applications of Flexible SNO-OCT Strained Alkynes and Their Use in Postpolymerization Modifications
Eileen G. Burke, Jennifer M. Schomaker
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01506

DOI: 10.1021/acs.joc.7b01506

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