Steps Towards the Total Synthesis of C60 Cages

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Steps Towards the Total Synthesis of C60 Cages
Eric Ballard Dr. Mitzel
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Precursors to My Research

• In 1977, Olof Wennerstrom used a 6-fold Wittig
  reaction to synthesize a C42H30 cage Simple and
  obtained high yields1

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Proposed Synthesis of C60 Cage

• Honed my skills by doing the Wittig
• First attempt successful so moved to more
  complicated reaction

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Trouble in Chemistryland

• This reaction proved to be more difficult
• After three failures, tried a new procedure

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Boosting Reactivity

• The reactivity of the Bromine was brought into
  question, so an In Situ Finkelstien with NaI was
  added to the procedure

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Further Tweaking

• The first step was refluxed for 2.5 hours yield
  had both the cis and trans isomers of
  1,4-distyrylbenzene
• Tried to further increase yield by refluxing
  longer but encountered a solvent leak problem and
  decided to move on

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1,4-distyrylbenzene
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Planning It Out

• The next step moved towards a large cage complex
• The plan

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Proposed Product
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Results

• Failed
• Failed
• In progress2

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References

• 1) Hoberg, H-E Thulin, b. Wennerstrom, O.
  Tetrahedron Lett. 1977, 931.
• 2) Buck, S. Johannes Ide, S. Walter, Org.
  Syntheses, CV 2, 130 (1943).

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Special Thanks

• Dr. Mitzel and his unique crew of researchers
• NSF REU for giving me money
• My awesome girlfriend, Wendy ?
• www.addictinggames.com