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Abstract A nitroso Diels–Alder (NDA) reaction between cyclopentadiene and an in situ generated nitroso compound leads to a new heterocyclic monomer for ring opening metathesis polymerization (ROMP) reactions. This monomer could be polymerized in the presence of Grubbs‐third generation initiator with good control overMnand decentÐvalues. The resulting isoxazolidine‐containing material could undergo further hydrogenation, deprotection, and modification with Dansyl chloride as well as ring opening to provide an amino‐and hydroxyl‐decorated “polyolefin.”more » « less