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Mechanistic Study of Photo-bis-Decarbonylation of Alpha-Diketones

Chakraborty, Saswata
http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1277056870

Abstract Details

2010, Master of Science (MS), Bowling Green State University, Chemistry.
The photo-bis-decarbonylation, the Strating-Zwanenberg reaction, of several α- diketones has been used to synthesize polyacenes, including heptacene. An effort has been made in this thesis to study the mechanism involved in the photo-bisdecarbonylation process. A range of diketones has been studied. Among these it is believed that Bicyclo[2.2.2]octene-2,3-dione (3) goes through an alleged allylic rearrangement before the decarbonylation resulting from biradical intermediates. The allylic product is highly unstable, and may be characterized only by absorption and IR spectroscopy. Aside from 3, none of the other polyacene precursors have shown this property. 2,3,9,10-Tetrabromo-6,13-dihydro-6,13-ethanopentacene-15,16-dione (14) exhibited dimer formation upon irradiation, and trapping of the biradical of 2,3,9,10- Tetra(2-methylphenyl)-6,13-dihydro-6,13-ethanopentacene-15,16-dione (13) with an acrylate monomer has been shown using MALDI-TOF. Other α-diketones provided no mass spectroscopic evidence when the trapping experiments were performed, explained by the short lifetime of the biradicals produced. The observations and results discussed will give us an insight into the photo-bis-decarbonylation process.
Dr. Douglas Neckers, PhD (Committee Chair)
Dr. Thomas Kinstle, PhD (Committee Member)
Dr, John Cable, PhD (Committee Member)
64 p.
Chemistry
acrylate; biradical; ¿¿¿¿-diketones; NMR; 1H NMR; NMR Spectra; irradiation

Recommended Citations

Citations

  • Chakraborty, S. (2010). Mechanistic Study of Photo-bis-Decarbonylation of Alpha-Diketones [Master's thesis, Bowling Green State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1277056870

    APA Style (7th edition)

  • Chakraborty, Saswata. Mechanistic Study of Photo-bis-Decarbonylation of Alpha-Diketones. 2010. Bowling Green State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1277056870.

    MLA Style (8th edition)

  • Chakraborty, Saswata. "Mechanistic Study of Photo-bis-Decarbonylation of Alpha-Diketones." Master's thesis, Bowling Green State University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=bgsu1277056870

    Chicago Manual of Style (17th edition)

bgsu1277056870
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This open access ETD is published by Bowling Green State University and OhioLINK.