Villafane, Louis
(2014)
Oxidative C-C Coupling Reactions of Benzofused Heterocycles Utilizing DDQ.
Master's Thesis, University of Pittsburgh.
(Unpublished)
Abstract
2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) mediated oxidative coupling chemistry that was previously developed in the Floreancig group for coupling with chromene cations has been expanded to include other benzofused heterocycles, including benzoxathioles, and is described herin. The reactivity of these cationic intermediates was utilized to rapidly furnish coupled benzofused heterocycles. The reactivity of the cationic intermediates was explored via addition of a number of nucleophiles and the electronics of the substrate were altered to determine the scope of the substrate in this type of transformation. In addition a one-pot method was developed to access spiro compounds, in the orthoester oxidation state, containing a synthetic handle for further manipulation.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
|
| Date: |
4 February 2014 |
| Date Type: |
Publication |
| Defense Date: |
14 December 2013 |
| Approval Date: |
4 February 2014 |
| Submission Date: |
6 December 2013 |
| Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
| Number of Pages: |
68 |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
MS - Master of Science |
| Thesis Type: |
Master's Thesis |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
Oxidation, Fragment Coupling, Heterocycles |
| Date Deposited: |
04 Feb 2014 16:07 |
| Last Modified: |
15 Nov 2016 14:16 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/20351 |
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