Abstract
Disiloxanetetraols are very useful synthetic precursors for various siloxane compounds. In addition, they are effective starting materials in sol–gel chemistry for the fabrication of well-defined structures. We herein described a facile single-step synthesis of disiloxanetetraols ([RSi(OH)2]2O) with various substituents (R = Pr, i-Pr, i-Bu, cyclopentyl, hexyl, cyclohexyl, Ph) by hydrolytic condensation of trichlorosilanes, where the reaction was quenched at an early stage. [PrSi(OH)2]2O has the smallest substituents among the disiloxanetetraols reported so far. The results of X-ray crystallography of [C5H9Si(OH)2]2O showed a supramolecular sheet structure formed by intermolecular hydrogen bonding. We also found that disiloxanetetraols and cyclotetrasiloxanetetraols with isobutyl groups can be synthesized from isobutyltrichlorosilane by simply changing the quenching time and reaction temperature.
References
Lickiss PD (1995) Adv Inorg Chem 42:147–262
Unno M, Alias SB, Arai M, Takada K, Tanaka R, Matsumoto H (1999) Appl Organomet Chem 13:303–310
Unno M, Alias SB, Saito H, Matsumoto H (1996) Organometallics 15:2413–2414
Unno M, Imai Y, Matsumoto H (2003) Silicon Chem 2:175–178
Zhang ZX, Hao J, Xie P, Zhang X, Han CC, Zhang R (2008) Chem Mater 20:1322–1330
Chandrasekhar V, Thirumoorthi R (2009) Inorg Chem 48:6236–6241
Andrianov KA, Izmailov BA, Petukhova ND (1976) Zh Obshch Khim 46:599–601
Hurkes N, Bruhn C, Celaj F, Piestschnig R (2014) Organometallics 33:7299–7306
Brown Jr JF, Vogt Jr LH (1965) J Am Chem Soc 87:4313–4137
Brown Jr JF, Slusarczuk GM (1964) J Org Chem 29:2809–2810
Seto I, Gunji T, Kumagai K, Arimitsu K, Abe Y (2003) Bull Chem Soc Jpn 76:1983–1987
Suyama K, Nakatsuka T, Gunji T, Abe Y (2007) J Organomet Chem 692:2028–2035
Unno M, Tanaka T, Matsumoto H (2003) J Organomet Chem 686:175–182
Lickiss PD, Lister SA, Redhouse AD, Wisener PD (1991) Chem Commun 173–174
Pescarmona PP, Van der waal JC, Maschmeyer T (2004) Chem Eur J 10:1657–1665
Kim JH, Han JS, Lim WC, Yoo BR (2007) J Ind Eng Chem 13:480
Toulokhonova I, Zhao R, Kozee M, West R (2001) Main Group Met Chem 24:737–744
Rulkens R, Coles MP, Tilley TD (2000) J Chem Soc Dalton Trans 627-628
Murugavel R, Bottcher P, Voigt A, Walawalker M. G, Roesky H. W, Parisini E, Teichert M, Noltemeyer M (1996) Chem Commun 2417-2418
Rickard CEF, Roper WR, Salter DM, Wright LJ (1992) J Am Chem Soc 114:9682–9683
Ren Z, Sun D, Li H, Fu Q, Ma D, Zhang J, Yan S (2012) Chem Eur J 18:4115–4123
Ren Z, Chen Z, Fu W, Zhang R, Shen F, Wang F, Ma Y, Yan S (2011) J Mater Chem 21:11306–11311
Perruchas S, Desboeufs N, Maron S, Goff XFL, Fagues A, Garcia A, Gacoin T, Boilot JP (2012) Inorg Chem 51:794–798
Yoshizawa M, Kusukawa T, Fujita M, Sakamoto S, Yamaguchi K (2001) J Am Chem Soc 123:10454–10459
Altomare A, Burla MC, Camalli M, Cascarano GL, Giacovazzo C, Guagliardi A, Moliterni AGG, Polidori G, Spagna R (1999) Sir97: a new tool for crystal structure determination and refinement. J Appl Crystallogr 32:115–119
Sheldrick GM (1997) SHELXS-97 and SHELXL-97, Program for the Refinement of Crystal Structures. University of Göttingen, Göttingen, Germany
Yamamoto S, Yasuda N, Ueyama A, Adachi H, Ishikawa M (2004) Macromolecules 37:2775–2778
Ito R, Kakihana Y, Kawakami Y (2009) Chem Lett 2009(38):364–365
Unno M, Suto A, Takada K, Matsumoto H (2000) Bull Chem Soc Jpn 73:215-220
Feher FJ, Schwab JJ, Soulivong D, Ziller JW (1997) Main Group Chem 2:123–132
Abe Y, Abe K, Watanabe M, Gunji T (1999) Chem Lett 28:259–260
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Highlights
-
Facile single-step synthesis of disiloxanetetraols ([RSi(OH)2]2O) with various substituents were realized.
-
Target compounds were obtained from substituted trichlorosilanes by the reaction in acetone-water at 0 °C for 1 hour.
-
No purification was necessary except work up, concentration, and washing by a solvent.
-
With this method, [PrSi(OH)2]2O that is the disiloxanetetraols with the smallest substituents was synthesized.
-
Crystallographic analysis for cyclopentyl-substituted [C5H11Si(OH)2]2O was performed and a sheet-like supramolecular structure was revealed.
Rights and permissions
About this article
Cite this article
Endo, H., Takeda, N. & Unno, M. Single-step synthesis of disiloxanetetraols. J Sol-Gel Sci Technol 89, 37–44 (2019). https://doi.org/10.1007/s10971-018-4635-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10971-018-4635-9