Synthesis of Crown Ethers & Stereochemistry of 1, 4-Ditertiarybutyl-1, 4-Dihydronaphthalene

Authors

Abdolreza-H-Hossein Nejad, Western Kentucky University

Publication Date

6-1978

Advisor(s) - Committee Chair

Norman Holy, Curits Wilkins, Robert Farina

Degree Program

Department of Chemistry

Degree Type

Master of Science

Abstract

A. Cyclization of ethylene oxide in the presence of transition metal salts was studied. Several reactions with different catalysts were tried and some of these reactions produced compounds which show only one sharp singlet in their NMR spectra. These products were also soluble in benzene. The solubility of potassium permanganate in this mixture suggests the presence of cyclic polyethers. In spite of the above observations, all attempts to liberate cyclic ethers from their metal complexes were unsuccessful.

B. In the second project, the stereochemistry of 1,4-ditertiarybuty1- 1,4-dihydronaphthalene was elucidated using ¹H and ¹³C NMR. For this purpose, other naphthalene and anthracene systems were used as model compounds. For cases in which no model systems were available, the angular dependence of coupling constants was used to estimate the coupling constants. The LAOCOON III computer program was implemented to produce the observed spectrum. It was determined that the dihydrobenzene ring in this molecule is nearly planar.

Disciplines

Chemistry | Physical Sciences and Mathematics

Recommended Citation

Nejad, Abdolreza-H-Hossein, "Synthesis of Crown Ethers & Stereochemistry of 1, 4-Ditertiarybutyl-1, 4-Dihydronaphthalene" (1978). Masters Theses & Specialist Projects. Paper 2688.
https://digitalcommons.wku.edu/theses/2688