Cationic Ring-Opening Polymerization of 1,3-Dehydroadamantanes

• Published in: Macromolecular symposia Vol. 240; no. 1; pp. 206 - 212
• Main Authors: Matsuoka, Shin-ichi, Ogiwara, Naoto, Uehara, Yosuke, Ishizone, Takashi
• Format: Journal Article Conference Proceeding
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.07.2006; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: 1,3‐dehydroadamantane; 3-adamantane; 3-dehydroadamantane; Aliphatic compounds; Applied sciences; Cationic; cationic polymerization; Chloroform; Degree of polymerization; Derivatives; Exact sciences and technology; Organic polymers; Physicochemistry of polymers; poly; poly(1,3‐adamantane); Polymerization; Preparation, kinetics, thermodynamics, mechanism and catalysts; ring-opening polymerization; Solvents; thermal stability; Weight loss; Ring opening polymerization; Molecular structure; Aliphatic polymer; Preparation; Polycyclic compound; Cationic polymerization; Experimental study; Solution polymerization; Thermal stability
• ISBN: 9783527317479; 3527317473
• ISSN: 1022-1360; 1521-3900
• DOI: 10.1002/masy.200650825

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.