Macrocyclic polyether sulfides have been prepared by reacting an oligoethylene glycol dichloride with a dithiol or sodium sulfide in ethanol. The following new compounds were prepared: 1-thia-(9-crown-3), 1,4-dithia-(9-crown-3), 1,4-dithia-(12-crown-4), 1,4,7-trithia-(12-crown-4), 1-thia-(18-crown-6), I,4-dithia-(18-crown-6), 1,7-dithia-(18-crown-6), 1,4,7-trithia-(18-crown-6), 1,7-dithia-(21-crown-7), 1,4,7-trithia-(21-crown-7). Four other previously reported macrocyclic polyether sulfides were also prepared. The symmetry of the nmr spectra of these compounds give added evidence for the proposed ring structures. The following subjects were presented and discussed: studies of cyclization by-products, dependence of cyclization yield on the size of the rings, high dilution principle and its application, medium-sized rings, effect of hetero-atoms on cyclization and melting point correlations. Also included in the dissertation is a detailed review of the syntheses of macrocyclic sulfides.
College and Department
Chemistry and Biochemistry
BYU ScholarsArchive Citation
Hui, Yau-Kwong Joseph, "Macrocyclic polyether sulfide syntheses, the preparation of thia-crown-3, 4, 6, and 7 compounds" (1974). Theses and Dissertations. 8236.
Ethers, Cyclic compounds