Bound Volume Number
Honors Capstone Project
Date of Submission
Arts and Science
the alkylation and subsequent cyclization reaction of endocyclic enol ethers
Capstone Prize Winner
Won Capstone Funding
Sciences and Engineering
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.
Mehdi, Sarah, "Investigation of the Tandem Alkylation-Cyclization of Endocyclic Enol Ethers for the Preparation of Unusual Oxygen Heterocycles" (2016). Syracuse University Honors Program Capstone Projects. 948.
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