Sarah Mehdi

Bound Volume Number

Volume III

Degree Type

Honors Capstone Project

Date of Submission

Spring 5-2016

Capstone Advisor

Nancy Totah

Capstone Major


Capstone College

Arts and Science

Audio/Visual Component


Audio/Visual Location

the alkylation and subsequent cyclization reaction of endocyclic enol ethers

Capstone Prize Winner


Won Capstone Funding


Honors Categories

Sciences and Engineering

Subject Categories



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.

Creative Commons License

Creative Commons Attribution 3.0 License
This work is licensed under a Creative Commons Attribution 3.0 License.

Included in

Chemistry Commons



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