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Origin of the regioselectivity in an intramolecular nucleophilic addition to arene chromium tricarbonyl complexes |
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| Authors: | Steven Chamberlin William D Wulff John V Muntean Arnold L Rheingold |
| Institution: | a Abbott Laboratories, Abbott Park, IL 60064, USA b Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA c Chemistry Sciences and Engineering Division, Argonne National Laboratory, 9700 South Cass Avenue, Argonne, IL 60439, USA d Department of Chemistry, University of California, San Diego, Urey Hall 5138, Mail Code 0358, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA |
| Abstract: | The source of the regioselectivity in the intramolecular nucleophilic addition of nitrile-stabilized carbanions to arene chromium tricarbonyl complexes was investigated for seven different substitution patterns on the arenes. All of the arenes are 1,4-dioxygenated and the substitution varies in the oxygen substituent and in the substituents of the arene carbons (hydrogen and alkyl). The regioselectivity is correlated with the preferred conformations of the chromium tricarbonyl group which in turn was determined by solution and solid-state 13C NMR spectroscopy, 1H NMR spectroscopy in solution as well as X-ray diffraction. In the four complexes analyzed by X-ray diffraction and the three complexes analyzed by solid-state 13C NMR spectroscopy, there was only one complex where it was found that the preferred conformation of the -Cr(CO)3 is different in solution than it is in the solid-state. |
| Keywords: | Arene chromium tricarbonyl Aromatic nucleophilic addition X-ray diffraction Solid-state 13C NMR spectroscopy Solution 13C NMR spectroscopy Regioselectivity |
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