Allyl sulfide monomers in ROMP: Access to polymers with high sulfur content

Outline for proposal

1 Summary (100 words, use project as a guide) – Goal is to test if allyl sulfides are reactive in ring-opening metathesis polymerisation (ROMP). Allyl sulfides are known to be reactive in olefin metathesis, but this reaction has never been done for ROMP. This reaction would supply polymers with high sulfur content, with potential uses in A, B, C, and others
2 Impact: An interesting chemical reactivity test (do allyl sulfides react in ROMP? And what catalysts are the most reactive? – fundamental questions). Also, the polymers are very useful in metal binding, water purification, etc etc.
3 AIMS & BACKGROUND
a Summarise overall goal and importance of project in 2-4 sentences.
b Background on olefin metathesis (scheme of the general reaction CM, RCM, ROMP). What is this reaction? How is it catalysed? What is the mechanism? (Focus on ruthenium catalysts). What are its uses? (1-2 pages)
c Background on allyl sulfides in olefin metathesis (see Chalker papers, especially Aust J. Chem). Explain how sulfur was previously thought to be generally incompatible with olefin metathesis. Explain how allyl sulfides promote metathesis (see JACS 2008 9642).
d Big question for this project: DO allyl sulfides work in ROMP? Is it faster than other (non-sulfur) ROMP reactions?
e AIMS: I) Make monomers (sulfur and non-sulfur) – draw monomers II) do ROMP with each monomer and several different metathesis catalysts – measure the rate, yield, molecular weight. III) Application of sulfur polymers (what application? (e.g. We will see if the polymer removes toxic metals from water – mercury, lead etc)
4 Research Project
a For aim 1 – use the Diels-Alder reaction to make the monomers. Show all targets and the reactions you will use to make them. These compounds will be characterised by NMR, mass spectrometry, IR and comparison to the literature values.
b For aim 2 – this key step in the project. First test CH2 vs O vs S and reaction with Grubbs-Hoveyda Second Generation Catalyst. Also show structure of other catalysts we will use (see catalysts 1, 5 and 6 and 11 in http://pubs.rsc.org/en/content/articlepdf/2015/cc/c4cc07932a). Run reactions at 1 mol% catalyst loading. Measure molecular weight by GPC. Calculate rate (by NMR) and yield for each substrate and catalyst.
c If we are able to carry out ROMP with allyl sulfides, need to find an application. Sulfur binds to metals such as mercury and lead. Test to see if the polymer can remove these from water. We will use ICP-MS to monitor if and how fast metals are removed from water.
5 Conclusion
a What is the point? What will we learn? Who will care? Why? Scientific impact? Why will society care?

draw scheme with structures (S vs O vs CH2). The CH2 version is commercially available. Need to synthesise the S and O version. We will use the Diels-Alder reaction

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