Date of Award
9-4-2012
Document Type
Thesis
Degree Name
Chemistry, MS
First Advisor
Michael Panigot
Committee Members
Allyn Ontko; Mark Draganjac
Call Number
LD 251 .A566t 2012 P32
Abstract
This thesis will focus on being able to synthesize an alkyne from an aldehyde, forming a dibromoalkene as an intermediate. This alkyne then can be converted to a stilbenoid in the future on reaction with alkyl lithium. Combretastatin A-4 and resveratrol are the stilbenoids, which have biological significance. These compounds have therapeutic value and are extracted from plants or fruits for their production. The chemical synthesis for these compounds from an economic point of view is very important. The Corey-Fuchs reaction was used to synthesize the dibromoalkenes. Literature cites use of triphenylphosphine as a reactant, but triisopropyl phosphite was used because of the poor solubility of the triphenylphoshine oxide which is hard to remove from the crude product. The formation of the dibromoalkene was detected using 1H NMR and the results showed the presence of dibromoalkene for all the aldehydes except for the Vanillin, Iso-Vanillin and Indole-3-carboxaldehyde.
Rights Management
This work is licensed under a Creative Commons Attribution 4.0 International License.
Recommended Citation
Padal, Dhanunjay N., "Aldehyde Bromination for Stilbenoid Syntheses" (2012). Student Theses and Dissertations. 883.
https://arch.astate.edu/all-etd/883
