Date of Award
Spring 4-29-2016
Track
Chemistry
Degree Type
Thesis
Degree Name
Master of Science in Chemical Sciences (MSCB)
Department
Chemistry
Committee Chair/First Advisor
Dr. Christopher W. Alexander
Committee Member
Dr. John Haseltine
Committee Member
Dr. Ellen Moomaw
Abstract
A broad and systematic study was conducted on synthetic methods to efficiently synthesize 1,3-S,O-esters, α-phosphonovinyl triflates, and α-alkynylphosphonates under mild reaction conditions. The master’s thesis is composed of two projects; the first project is titled “Synthesis of 1,3-S,O-Esters” and the second project is titled “Synthesis of α-Phosphonovinyl Triflates and α-Alkynylphosphonates.” The first project outlines a synthetic route to conveniently prepare novel α-functionalized 1,3-S,O-esters via an acid-promoted hydrolysis of α-functionalized α-oxoketene dimethylthioacetals. The second project, unrelated to the first project, primarily focuses on extensive synthetic methodology developed to prepare novel β-functionalized α-phosphonovinyl triflates and display their synthetic application by performing a base-promoted β-elimination to produce β-functionalized α-alkynylphosphonates.