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Aryl acetylene substituent effects : the synthesis and application of biaryls

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dc.contributor.advisor Carter, Richard G.
dc.creator Naffziger, Michael R.
dc.date.accessioned 2010-12-30T22:13:59Z
dc.date.available 2010-12-30T22:13:59Z
dc.date.copyright 2010-07-07
dc.date.issued 2010-12-30
dc.identifier.uri http://hdl.handle.net/1957/19650
dc.description Graduation date: 2011 en_US
dc.description.abstract The work described herein details the synthesis and application of biphenyls that probe the effects of hydrogen, Cl / Br, and methyl substituents on the aryl ring of the terminal acetylenic carbon. From this work, we successfully developed the rapid synthesis of phenyl acetylenes in 3-4 steps from inexpensive commercially available materials. Using these mild conditions, a wide host of functionalized acetylenes has been easily achieved, avoiding complex and or difficult synthetic transformations With the functionalized acetylenes in had, we demonstrated that the subtle change from hydrogen to either methyl or halogen imparts diverse results when subjected to [4+2] or [3+2] cycloadditions. This knowledge has helped to explain other unexplained observations from previous work within this project. These biphenyls were then further investigated by performing various synthetically useful functional group transformations and comparing the differences the substituents have on the corresponding reaction. Noteworthy is the total synthesis of siamenol, a carbazole isolated from the bark of Murriaya siamensis, where the key carbazole forming step is effected by the substituents about the molecule in the synthesis of siamenol derivatives. en_US
dc.language.iso en_US en_US
dc.subject cycloaddition en_US
dc.subject Diels-Alder en_US
dc.subject 4+2 en_US
dc.subject 3+2 en_US
dc.subject triazole en_US
dc.subject isoxazole en_US
dc.subject microwave en_US
dc.subject palladium en_US
dc.subject Suzuki en_US
dc.subject siamenol en_US
dc.subject Cadogan en_US
dc.subject carbazole en_US
dc.subject aryl acetylene en_US
dc.subject chloro acetylene en_US
dc.subject bromo acetylene en_US
dc.subject methyl acetylene en_US
dc.subject Ohira en_US
dc.subject Bestman en_US
dc.subject biaryl formation en_US
dc.subject biaryl functionalization en_US
dc.subject biaryl en_US
dc.subject biphenyl en_US
dc.title Aryl acetylene substituent effects : the synthesis and application of biaryls en_US
dc.type Thesis/Dissertation en_US
dc.degree.name Master of Science (M.S.) in Chemistry en_US
dc.degree.level Master's en_US
dc.degree.discipline Science en_US
dc.degree.grantor Oregon State University en_US
dc.contributor.committeemember Kong, Wei
dc.contributor.committeemember Gable, Kevin
dc.contributor.committeemember Coakley, James


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