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.

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