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Mechanistic Study and Application of Decarbonylation of Cyclopropenone

Zichun Ren
Zichun Ren
Graduate Student, Department of Chemistry
University of Georgia
Chemistry Building, Room 400
Organic Seminar

Cyclopropenone is an organic compound consisting of cyclopropene framework with a ketone functional group. It has been found in various natural compounds. Cyclopropenone can also undergo different kinds of reactions but most of the reactions can be categorized to nucleophilic attack and decarbonylation. Although photodecarbonylation is the one of the most common reaction of cyclopropenones, there is very little agreement in the literature on the photoactivation mechanism. A multitude of studies and techniques have been employed toward understanding their photodissociation to cycloalkynes. In this seminar, we will introduce method using transient absorbance spectroscopy to study the mechanism of Decarbonylation of photooxadibenzocyclooctyne. Decarbonylation of photo-ODIBO under 321 nm and 350 nm were studied and we proposed different mechanism of photoactivation under these two conditions. Then we explored the biological and genomic applications of cyclopropenone derivatives using photo-ODIBO or photo-ADIBO for in-situ sequencing. Last but not the least, we synthesized photo-ODIBO-Biotin and try to explore the feasibility of irradiation of photo-ODIBO with visible light.

Applications and reactions of Decarbonylation of Cyclopropenone

References

  1. McNitt, C. D.; Popik, V. V. Organic & Biomolecular Chemistry 2012, 10, 8200.
  2. Nainar, S.; Kubota, M.; McNitt, C.; Tran, C.; Popik, V. V.; Spitale, R. C. Journal of the American Chemical Society 2017, 139, 8090.
  3. Shenje, L.; Thompson, W.; Ren, Z.; Lin, N.; Popik, V.; Ullrich, S. The Journal of Chemical Physics 2021, 154, 074302.
  4. Poloukhtine, A. A.; Mbua, N. E.; Wolfert, M. A.; Boons, G.-J.; Popik, V. V. Journal of the American Chemical Society 2009, 131, 15769.
  5. Poloukhtine, A.; Popik, V. V. The Journal of Physical Chemistry A 2006, 110, 1749.

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