A Cyclophane-Based Approach to [n]Cycloparaphenylenes and an Allylic Arylation Strategy for Regioselective Triphenylene Synthesis
Metadata Field | Value | Language |
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dc.contributor.advisor | Bradley Merner | |
dc.contributor.author | Caroline Merryman | |
dc.date.accessioned | 2019-04-17T16:30:51Z | |
dc.date.available | 2019-04-17T16:30:51Z | |
dc.date.issued | 2019-04-17 | |
dc.identifier.uri | http://hdl.handle.net/10415/6621 | |
dc.description.abstract | CHAPTER 1 Synthesis of functionalized p-terphenyl-containing macrocycles as key intermediates in the synthesis of functionalized [n]CPPs Strategically designed, substituted para-terphenyl-containing macrocycles are explored as possible key intermediates in the synthesis of functionalized [n]cycloparaphenylenes. These para-terphenyl-containing macrocycles are prepared via a streamlined synthesis, proceeding through a macrocyclic 1,4-diketone, that has been previously reported by our group. This strategy does not employ the use of cross-coupling reactions, and is, therefore, tolerant of the incorporation of the functional groups necessary to prepare [n]CPPs from these para-terphenyl-containing macrocycles. CHAPTER 2 Toward the Synthesis of [4]Cycloparaphenylene Synthetic routes towards the next smallest, yet-to-be-synthesized [4]CPP are explored. These strategies aim to employ a macrocyclic 1,4-diketone as a key intermediate. The paracyclophane-based strategy aims to bypass the challenges expected with the macrocyclization of such a highly strained molecule. CHAPTER 3 Synthesis of regioselectively functionalized triphenylenes via allylic arylation A series of unsymmetric triphenylene systems are reported. The final two steps of these syntheses are an allylic arylation onto a cyclohex-2-ene-1,4-diol-based system and subsequent aromatization. This synthetic process has been streamlined and applied to both electron rich and electron deficient systems. Selected triphenylenes are explored as substrates for further pi-extension. | en_US |
dc.rights | EMBARGO_NOT_AUBURN | en_US |
dc.subject | Chemistry and Biochemistry | en_US |
dc.title | A Cyclophane-Based Approach to [n]Cycloparaphenylenes and an Allylic Arylation Strategy for Regioselective Triphenylene Synthesis | en_US |
dc.type | Master's Thesis | en_US |
dc.embargo.length | MONTHS_WITHHELD:12 | en_US |
dc.embargo.status | EMBARGOED | en_US |
dc.embargo.enddate | 2020-04-15 | en_US |