Macrocyclic polycther sulfide syntheses. The preparation of thia‐crown‐5, 6 and 7 compounds

Jerald S. Bradshaw, J. Y. Hui, Yin Chan, Barry L. Haymore, Reed M. Izatt, Jeppe Christensen

Journal of Heterocyclic Chemistry · 1974 · 68 citations · 9 references

Concepts

Abstract

Abstract Macroeyclic polyether sulfides have been prepared by reacting an oligoethylene glycol dichloride with a dimercaptan or sodium sulfide as reported in a previous paper (6). The following new compounds were prepared: 1,4,7‐trithia(15‐crown‐5) (1); 1,4,10‐trithia(15‐crown‐5) (II): 1,4,7,10‐tetrathia(15‐crown‐5) (III); I‐thia(18‐crown‐6) (IV); 1,4‐dithia(18‐crown‐6) (V); 1,7‐dithia(18‐crown‐6) (VI); 1,4,7‐trithia(18‐crown‐6) (VII); 1,7‐dithia(21‐crown‐7) (VIII); and 1,4,7‐trithia(21‐crown‐7) (IX). The melting points of these and previously reported thia‐crown compounds correlate with their structures. X‐ray analyses of two thia‐crown compounds indicate that the large sulfur atoms are directed away from the center of the ring.

References

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