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Asymmetric Synthesis of the 3-TOSU Monomer
Abstracts of Papers of the American Chemical Society
  • R. A. A. Upul Ranaweera
  • S. Subramani
  • Nicholas Jentsch
  • Thomas P. Schuman, Missouri University of Science and Technology
Abstract

A surface reactive, organic spiroorthoester monomer ligand, [3-(9,9-diethyl-1,5,7,11-tetraoxa-spiro[5,5]undec-3-yl)-propyl]-trimethoxysilane (3-TOSU), was synthesized at a 0.1 mole scale and, with the reaction intermediates, characterized using infrared and 1H and 13C NMR spectroscopies, and mass spectrometry (GC-MS). An improved procedure for the synthesis of 3-TOSU via the corresponding thiocarbonate is described. The 3-TOSU monomer can be used to functionalize nanoparticles, whose incorporation and cure into a resulting solid 0‑3 composite can produce materials of reduced polymerization stress/volume shrinkage, and bone cements of low cell toxicity and higher strength. The objective was to develop a well-characterized synthetic route to a high quality product of the 3-TOSU chemical structure.

Meeting Name
246th National Meeting of the American-Chemical-Society (2013: Sep. 8-12, Indianapolis, IN)
Department(s)
Chemistry
Document Type
Article - Conference proceedings
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2013 American Chemical Society (ACS), All rights reserved.
Publication Date
9-12-2013
Disciplines
Citation Information
R. A. A. Upul Ranaweera, S. Subramani, Nicholas Jentsch and Thomas P. Schuman. "Asymmetric Synthesis of the 3-TOSU Monomer" Abstracts of Papers of the American Chemical Society (2013) ISSN: 0065-7727
Available at: http://works.bepress.com/thomas-schuman/70/