Cationic ring-opening polymerization behavior of a five-membered cyclic thiocarbonate having a spiro-linked adamantane moiety

作者: Nobukatsu Nemoto , Yoshinori Ito , Takeshi Endo

DOI: 10.1002/POLA.10617

关键词:

摘要: This work deals with the synthesis and cationic ring-opening polymerization behavior of a novel five-membered cyclic thiocarbonate bearing spiro-linked adamantane moiety, tricyclo[3.3.1.1 3,7 ]decane-2-spiro-4'-(1',3'-dioxolane-2'-thione) (TC2). The TC2 did not proceed trifluoromethanesulfonic acid, methyl trifluoromethanesulfonate, triethyloxonium tetrafluoroborate (Et 3 OBF 4 ), boron trifluoride etherate (BF OEt 2 titanium tetrachloride, or iodide as initiator, presumably because steric hindrance moiety. However, copolymerization five- six-membered thiocarbonates, that is, 1,3-dioxolane-2-thione, 1,3-dioxane-2-thione, 5-methyl-1,3-dioxane-2-thione, 5,5-dimethyl-1,3-dioxane-2-thione, initiated by BF Et , proceeded to afford corresponding copolymer via selective direction. increase in feed ratio increased unit derived from copolymer; however, molecular weight decreased.

参考文章(23)
Yoshio Imai, Mitsuru Ueda, Masahiro Ii, Synthesis of aromatic polysulfonates by phase-transfer-catalysed polycondensation with crown ethers Macromolecular Chemistry and Physics. ,vol. 179, pp. 2085- 2087 ,(1978) , 10.1002/MACP.1978.021790822
Nobukatsu Nemoto, Xiaoyu Xu, Fumio Sanda, Takeshi Endo, Cationic Ring-Opening Polymerization of Cyclic Monothiocarbonates: Varying the Polymer Main Chain by Neighboring Group Participation Macromolecules. ,vol. 34, pp. 7642- 7647 ,(2001) , 10.1021/MA010653F
Frank Norton Jones, S. Andreades, Ethylene thionocarbonate and 1,3-oxathiolane-2-thione Journal of Organic Chemistry. ,vol. 34, pp. 3011- 3014 ,(1969) , 10.1021/JO01262A047
A P Khardin, S S Radchenko, Polymeric Derivatives of Adamantane Russian Chemical Reviews. ,vol. 51, pp. 272- 285 ,(1982) , 10.1070/RC1982V051N03ABEH002840
Nobukatsu Nemoto, Fumio Sanda, Takeshi Endo, Controlled Cationic Ring-Opening Polymerization of Monothiocarbonate Macromolecules. ,vol. 33, pp. 7229- 7231 ,(2000) , 10.1021/MA000760U
M.R. Pixton, D.R. Paul, Gas transport properties of adamantane-based polysulfones Polymer. ,vol. 36, pp. 3165- 3172 ,(1995) , 10.1016/0032-3861(95)97880-O
Hisamitsu Kameshima, Nobukatsu Nemoto, Fumio Sanda, Takeshi Endo, Cationic Ring-Opening Polymerization of Five-Membered Cyclic Thiocarbonate Bearing an Adamantane Moiety via Selective Ring-Opening Direction Macromolecules. ,vol. 35, pp. 5769- 5773 ,(2002) , 10.1021/MA012094I
Toshikazu Takata, Takeshi Endo, Recent advances in the development of expanding monomers: Synthesis, polymerization and volume change Progress in Polymer Science. ,vol. 18, pp. 839- 870 ,(1993) , 10.1016/0079-6700(93)90019-9
Mitsumoto Murayama, Fumio Sanda, Takeshi Endo, Anionic Ring-Opening Polymerization of a Cyclic Carbonate Having a Norbornene Structure with Amine Initiators Macromolecules. ,vol. 31, pp. 919- 923 ,(1998) , 10.1021/MA970878J