Synthesis of Polypropellanes via Ring-Opening Polymerization or Coupling Reaction

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Cationic ring-opening polymerizations of [3.3.1]propellane derivatives, 1,3-dehydroadamantane (1)and 5-butyl-1,3-dehydroadamantane (2), were carried out with CF_3SO_3H in CH_2Cl_2 at 0℃ for 6-42 h. The central σ-bonds in 1 and 2 were exclusively opened to afford novel poly([3.3.1]propellane)s, poly(1,3-adamantane)s, in good to quantitative yields. The resulting poly(2)possessing flexible butyl substituent was soluble in chloroform, THF, and 1,2-dichlorobenzene, and the degree of polymerization was estimated to be greater than 30, while the poly(1)was hardly soluble in the common organic solvents. All aliphatic poly(1)and poly(2)showed high thermal stability, whose 10% weight loss temperatures were 421 and 486℃, respectively.