| Autor: |
Tararov, V. I., Savel'eva, T. F., Struchkov, Yu. T., Pisarevskii, A. P., Raevskii, N. I., Belokon, Yu. N. |
| Zdroj: |
Russian Chemical Bulletin; March 1996, Vol. 45 Issue: 3 p600-609, 10p |
| Abstrakt: |
Regioselectivity and diastereoselectivity of the addition of BrCCl3 to (R)-3-(E)-cinnamoyl-4-phenyloxazolidin-2-one (1) and (R)-3-(E)-acryloyl-4-phenyloxazolidin-2-one (2) catalyzed by Fe(CO)5 or initiated with benzoyl peroxide were investigated. Stereochemistry of the reaction of BrCCl3 with the a-complexes (4R,aS,ßS)-?2-(3-(E)-cinnamoyl-4-phenyl-oxazolidin-2-one)irontetracarbonyl (3a) and (4R,aR)-?2-(3-acryloyl-4-phenyloxazolidin-2-one)irontetracarbonyl (4b) was also studied. The results obtained allow the following conclusions to be drawn: (1) the thermal Kharasch reaction catalyzed by Fe(CO)5 proceeds by a redox catalysis mechanism; (2) iron (in any of its oxidation states) is not coordinated to olefins in the transition state of the reaction; (3) the transfer of the halogen atom on the radical adduct probably occurs inside a radical-iron cation pair. |
| Databáze: |
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| Externí odkaz: |
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