Copolymerization of 1,3-Dehydroadamantane with Vinyl Monomers

Significance

Copolymerization of 1,3-dehydro­adamantane 1 and electron-deficient vinyl monomer 2 or 3, in the absence of any initiator, occurred at room temperature, providing alternating copolymers in 28-88% yield. The failed copolymerizations of 1 with isobutyl vinyl ether and styrene indicate the high electron density of a central σ-bond in a strained [3.3.1] propellane derivative 1. The alternating copolymers were characterized by NMR spectroscopy and MALDI-MS. DSC and TGA measurements revealed the high thermostability of the copolymers containing bulky and strain-free adamantane fragments.