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
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.