Cationic Ring-Opening Polymerization of 1,3-Dehydroadamantanes |
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Authors: | Shin-ichi Matsuoka Naoto Ogiwara Yosuke Uehara Takashi Ishizone |
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Institution: | Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1-H-119, Ohokayama, Meguro-ku Tokyo 152-8552 Japan |
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Abstract: | Ring-opening polymerizations of 3.3.1]propellane derivatives, 1,3-dehydroadamantane ( 1 ) and 5-butyl-1,3-dehydroadamantane ( 2 ), were carried out with CF3SO3H in CH2Cl2 at 0 °C 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 52–95% 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, their 10% weight loss temperatures were 421 and 486 °C, respectively. |
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Keywords: | 1 3-dehydroadamantane cationic polymerization poly(1 3-adamantane) ring-opening polymerization thermal stability |
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