The Synthesis of Novel Cyclohexyne Precursors for an Intramolecular Pauson-Khand Type Reaction
| dc.contributor.advisor | Martin, Stephen F. | |
| dc.creator | Etkind, Samuel I. | |
| dc.date.accessioned | 2017-05-03T17:57:16Z | |
| dc.date.available | 2017-05-03T17:57:16Z | |
| dc.date.issued | 2017 | |
| dc.description.abstract | Strained cycloalkynes, particularly cyclohexyne and cyclopentyne, are interesting synthetic intermediates that have largely been overlooked in organic synthesis. In addition, the Pauson-Khand reaction is a formal [2+2+1] cycloaddition that utilizes an alkene, an alkyne, and carbon monoxide. The use of strained cycloalkynes in the Pauson-Khand reaction has been surveyed, but it has not been performed successfully for cyclohexyne and cyclopentyne containing substrates. Design and optimization of such a reaction could lead to the swift synthesis of a polycyclic scaffold that is found in many natural products, many of which have not been synthesized. This thesis presents several approaches to a new class of vinyl triflates that could serve as cyclohexyne precursors for the Pauson-Khand reaction. While only a few cyclohexyne precursors were successfully synthesized, a synthetic route is presented that can access this class of molecules in moderate yield over three steps. In addition, use of these cyclohexyne precursors in the Pauson-Khand reaction led to the formation of the desired polycyclic product. | en_US |
| dc.description.department | Chemistry | en_US |
| dc.identifier | doi:10.15781/T2TB0Z13F | |
| dc.identifier.uri | http://hdl.handle.net/2152/46675 | |
| dc.language.iso | eng | en_US |
| dc.relation.ispartof | Honors Theses | en_US |
| dc.rights.restriction | Open | en_US |
| dc.subject | organic chemistry | en_US |
| dc.subject | synthesis | en_US |
| dc.subject | Pauson-Khand | en_US |
| dc.subject | Cycloalkyne | en_US |
| dc.subject | Cyclohexyne | en_US |
| dc.title | The Synthesis of Novel Cyclohexyne Precursors for an Intramolecular Pauson-Khand Type Reaction | en_US |
| dc.type | Thesis | en_US |