Bound Volume Number
Volume III
Degree Type
Honors Capstone Project
Date of Submission
Spring 5-2016
Capstone Advisor
Nancy Totah
Capstone Major
Chemistry
Capstone College
Arts and Science
Audio/Visual Component
no
Audio/Visual Location
the alkylation and subsequent cyclization reaction of endocyclic enol ethers
Capstone Prize Winner
no
Won Capstone Funding
no
Honors Categories
Sciences and Engineering
Subject Categories
Chemistry
Abstract
The purpose of this research is to study the alkylation and subsequent cyclization reaction of endocyclic enol ethers such as 2H-dihydropyran. This sequence is expected to yield oxygen heterocycles whose structures represent unique scaffolds with promising functionality.
A series of trichloroacetimidates were selected for the direct alkylation of 2H-dihydropyran. Following the alkylation, the addition of acid was expected to induce an intramolecular cyclization reaction that would yield the desired oxygen heterocycles. This stepwise scheme would then be converted into a tandem process in which the reaction would be expected to proceed in a single pot.
Studies showed that the alkylation step of the reaction was unreliable, often yielding an unexpected compound as the major product or leading to the formation of vast amounts of side products, and very little desired product. In future studies optimization of the alkylation step in regards to the selected trichloracetimidates could prove useful in achieving the formation of oxygen heterocycles as the end goal.
Recommended Citation
Mehdi, Sarah, "Investigation of the Tandem Alkylation-Cyclization of Endocyclic Enol Ethers for the Preparation of Unusual Oxygen Heterocycles" (2016). Honors Capstone Projects - All. 948.
https://surface.syr.edu/honors_capstone/948
Creative Commons License
This work is licensed under a Creative Commons Attribution 3.0 License.
