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Catalytic cyclooligomerization of thietane by trirhenium cluster complexes: A new route to polythiaether macrocycles

Journal Article · · Journal of the American Chemical Society; (United States)
DOI:https://doi.org/10.1021/ja00102a022· OSTI ID:7080198
;  [1]
  1. Univ. of South Carolina, Columbia, SC (United States)

The trirhenium complex Re[sub 3](CO)[sub 10] [[mu]-SCH[sub 2]CH[sub 2]]([mu]-H)[sub 3] (1) reacts with dimethyl sulfide by a ring opening addition to the bridging thietane ligand to yield the zwitterionic complex Re[sub 3](CO)[sub 10][[mu]-SCH[sub 2]CH[sub 2]CH[sub 2]SMe[sub 2]]([mu]-H)[sub 3] (2) in 48% yield that contains a sulfonium-substituted thiolate ligand bridging an edge of the cluster. The structure of 2 was established by a single-crystal X-ray diffraction analysis. In this report, the results of our studies of the reactions of 1 with the thiaethers Me[sub 2]S and thietane, itself, are described. It is demonstrated that these thiaethers also produce ring opening of the bridging thietane ligand in 1, but in the case of thietane, a series of ring-opening coupling reactions occurs that is concluded by cyclization processes that yield polythiaether macrocycles. Indeed, the ring-opening cyclization can be performed catalytically under suitable conditions to yield the macrocycles in a free state in substantial amounts. 13 refs., 2 figs., 6 tabs.

OSTI ID:
7080198
Journal Information:
Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 116:23; ISSN JACSAT; ISSN 0002-7863
Country of Publication:
United States
Language:
English