Abstract
1,3,5-Trimethoxy-1,3,5-triisopropylcyclotrisiloxane (2) was prepared from 1,3,5-triisopropyl-1,3,5-tri-o-tolylcyclotrisiloxane—(1) according to three kinds of methods as follows: the dearylchlorination of 1 using HCl/AlCl3, which led to prepare 2 includes a very slight amount of aluminum species as impurities, the dearylbromination using Br2, which simultaneously brought unnecessary bromination without isolated 2, and the dearylation using TfOH, which efficiently gave 2 of a high purity without metals of contamination.
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Yamaoka, K., Yoshizako, Y., Kato, H., Tsukiyama, D., Terai, Y., Fujiwara, Y.: Room-temperature plasma-enhanced chemical vapor deposition of SiOCH films using tetraethoxysilane. Phys. B Condens. Matter 376–377, 399–402 (2006)
Yang, C.S., Yu, Y.H., Lee, K.-M., Lee, H.-J., Choi, C.K.: Investigation of low dielectric carbon-doped silicon oxide films prepared by PECVD using methyltrimethoxysilane precursor. Thin Solid Films 506–507, 50–54 (2006)
Kohmura, K., Tanaka, H., Oike, S., Murakami, M., Ono, T., Seino, Y., Kikkawa, T.: Effect of plasma treatment and TMCTS vapor annealing on the reinforcement of porous low-k films. Mater. Res. Soc. Symp. Proc. 863, 67–72 (2005)
Corey, J.Y.: Dehydrogenative coupling reactions of hydrosilanes. In: Larson, G.L. (ed.) Advances In Silicon Chemistry, vol. 1, pp. 327–387. JAI Press, Greenwich (1991)
Gunji, Y., Yamashita, Y., Ikeno, T., Yamada, T.: Convenient and selective preparation of mono-alkoxyphenylsilanes from phenylsilane and alcohols. Chem. Lett. 35(7), 714–715 (2006)
Crandall, J.K., Morel-Fourrier, C.: Siloxanes from the hydrolysis of isopropyltrimethoxysilane. J. Organomet. Chem. 489, 5–13 (1995)
Unno, M., Kishimoto, Y., Matsumoto, H.: Triisopropylcyclotrisiloxanetriol: an unprecedented cyclic siloxanetriol with relatively small substituents. Organometallics 23, 6221–6224 (2004)
Unno, M., Chang, S., Matsumoto, H.: cis-trans-cis-Tetrabromotetramethylcyclotetrasiloxane: a versatile precursor of ladder silsesquioxanes. Bull. Chem. Soc. Jpn. 78, 1105–1109 (2005)
Fukazawa, A., Tsuji, H., Tamao, K.: Skeletal rearrangement of a bicyclic 1,3-diphenyltrisilane during acid-induced dephenylation reactions. Silicon Chem. 3, 157–163 (2005)
Fossum, E., Gordon-Wylie, S.W., Matyjaszewski, K.: Identification of the stereoisomers of 1,2,3,4-tetramethyl-1,2,3,4-tetraphenylcyclotetrasilane. Organometallics 13, 1695–1698 (1994)
Toskas, G., Besztercey, G., Moreau, M., Masure, M., Sigwalt, P.: Cationic polymerization of hexamethylcyclotrisiloxane by trifluoromethanesulfonic acid and its derivatives. 2. Reaction involving activated trifluoromethanesulfonates. Macromol. Chem. Phys. 196, 2715–2735 (1995)
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Ochiai, M., Akiyama, E., Ueno, T. et al. Comparative study on syntheses of 1,3,5-trimethoxy-1,3,5-triisopropylcyclotrisiloxane. Silicon Chem 3, 307–312 (2008). https://doi.org/10.1007/s11201-008-9033-7
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DOI: https://doi.org/10.1007/s11201-008-9033-7