Disclosed herein are degradable materials comprising the reaction product of an oxanorbornadiene crosslinker or derivative thereof and a multivalent nucleophile-terminated compound, wherein the reaction product is a degradable elastic solid capable of entraining cargo. Also disclosed herein are degradable materials comprising a polymeric and hyperbranched crosslinked material made with oxanorbornadiene linkage that can be activated for cleavage at a predetermined rate by addition of a nucleophile. Also disclosed herein are methods of making and using the same.