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Regioselective Electrolytic 5,8-Difluorination Of Quinolines, Sean P. Spurlin
Regioselective Electrolytic 5,8-Difluorination Of Quinolines, Sean P. Spurlin
Honors College Theses
Over the past decade, synthesis of organofluorine compounds has become a mainstream research focus. The introduction of fluorine uniquely affects the biological properties of organic molecules such as making them more bioavailable, lipophilic and metabolically stable, and possibly increase the strength of a compound’s interactions with a target protein. Approximately 30% of agrochemicals and 20% of pharmaceuticals contain fluorine, including commonly prescribed drugs such as Lipitor, Lexapro and Prozac. This work describes the development of a new methodology to incorporate fluorine into organic compounds. Our new method involves a regioselective electrochemical 5,8-difluorination of quinolines using HF:pyridine as both the reagent …
Synthesis Of Multifunctional Polyacrylates And A Binding Group To Hemoglobin For The Treatment Of Traumatic Brain Injuries, Marina Michaud
Synthesis Of Multifunctional Polyacrylates And A Binding Group To Hemoglobin For The Treatment Of Traumatic Brain Injuries, Marina Michaud
Honors College Theses
Hemoglobin based oxygen carriers (HBOCs) hold promise as an effective emergency treatment of severe traumatic brain injuries (TBI). In the latest generation of HBOCs, polynitroxyl-pegylated hemoglobin (PNPH), cell-free hemoglobin is modified with TEMPO and PEG which reduce the toxicities associated with earlier generations of HBOCs. In our efforts to optimize the economic and therapeutic impacts of PNPH’s we have synthesized polydimethylaminoethyl methacrylate (poly-DMAEMA) under controlled living conditions via reverse addition-fragmentation chain transfer (RAFT) polymerization. The poly-DMAEMA was then successfully functionalized via quaternization of its NMe2 groups using chloroacetate derivatives of the TEMPO and PEG. This process was quantitative and …
Iodine-Initiated Hydration Of Internal Alkynes, Nicholas J. Shuber, Karelle Aiken
Iodine-Initiated Hydration Of Internal Alkynes, Nicholas J. Shuber, Karelle Aiken
Honors College Theses
The iodine-initiated hydration of internal alkynes is a novel, green, and inexpensive synthetic pathway in comparison with the commonly used transition metal catalyzed reactions. This can be a useful alternative in many fields, academic or industrial. This experimental design has been used successfully on terminal alkynes and is now being extended to internal alkynes. Through systematic probing of the reaction conditions, we have gleaned sufficient information to determine a strong mechanistic hypothesis based on neighboring group participation. Here in, we will report our result with a series of internal, keto alkynes reacted under ambient conditions with iodine in “wet” solvent. …