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Chemical compound From Wikipedia, the free encyclopedia
Chlorobis(cyclooctene)rhodium dimer is an organorhodium compound with the formula Rh2Cl2(C8H14)4, where C8H14 is cis-cyclooctene. Sometimes abbreviated Rh2Cl2(coe)4, it is a red-brown, air-sensitive solid that is a precursor to many other organorhodium compounds and catalysts.
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3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.152.028 |
PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |
C32H56Cl2Rh2 | |
Molar mass | 717.50 |
Appearance | red-brown solid |
Hazards | |
GHS labelling: | |
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H302, H312, H315, H319, H332, H335 | |
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The complex is prepared by treating an alcohol solution of hydrated rhodium trichloride with cyclooctene at room temperature.[1] The coe ligands are easily displaced by other more basic ligands, more so than the diene ligands in the related complex cyclooctadiene rhodium chloride dimer.
C-H activation is often catalyzed by chlorobis(cyclooctene)rhodium dimer as demonstrated in the synthesis of a strained bicyclic enamine.[2]
The synthesis of a mescaline analogue involves enantioselective annulation of an aryl imine via a C-H activation.[3]
The total synthesis of lithospermic acid employs "guided C-H functionalization" late stage to a highly functionalized system. The directing group, a chiral nonracemic imine, is capable of performing an intramolecular alkylation, which allows for the rhodium-catalyzed conversion of imine to the dihydrobenzofuran.[4]
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