Catalytic cyclo-oligomerization of {beta}@-propiothiolactone by a dirhenium complex. A convenient route to new polythiolactone macrocycles
- Univ. of South Carolina, Columbia, SC (United States)
In recent studies, we have shown that Re{sub 2}(CO){sub 9}(NCMe)(1) can serve as a catalyst for the macrocyclization of thietanes. We have now found that 1 also activates {beta}@-propiothiolactone, SCH{sub 2} CH{sub 2}C=O(2), toward opening of the heterocyclic ring under mild conditions. The known polymer (SCH{sub 2}CH{sub 2}C=O){sub n}{sup 2} (55% yield) and a mixture of new cyclooligomers (SCH{sub 2}-CH{sub 2}C=O){sub n}, two of which,1,5,9,13-tetrathiacyclohexadecane-2,6,10,14-tetrone (3) (22% isolated yield) and 1,5,9,13,17, 21-hexathiacyclotetracosane-2,6,10,14,18,22-hexone (4), n = 6(2% isolated yield), have been isolated and characterized crystallographically. Recent studies have provided some of the first examples of polythiolactones from acyclic precursors. These molecules all exhibit head-to-head/tail-to-tail orientations of the thiolactone groupings(A). Compounds 3 and 4 are the first members of a new family of head-to-tail oriented polythiolactones B that have a clear and demonstrated potential to exhibit new supramolecular properties. 8 refs., 2 figs.
- OSTI ID:
- 405322
- Journal Information:
- Journal of the American Chemical Society, Vol. 118, Issue 39; Other Information: PBD: 2 Oct 1996
- Country of Publication:
- United States
- Language:
- English
Similar Records
Facile alkyne coupling reactions in dirhenium carbonyl complexes
Catalytic cyclooligomerization of thietane by dirhenium carbonyl complexes