The selective functionalization of saturated hydrocarbons. Part 47. Investigation of the size of the reagent involved in the FeII–FeIV manifold
✍ Scribed by Derek H.R. Barton; Franck Launay
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 397 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Competition experiments between cyclohexane and various aromatic substrates have been carried out in pyridine-acetonitrile in order to ascertain the steric requirements of the FeI~-H202 reagent in comparison with the Fem-H202 reagent already studied. The latter is distinctly larger and much less reactive than the fon'ner. Although these results might indicate that the Fen-H202 reagent is simply the hydroxyl radical, the chemistry observed is strictly dependent on the presence of picolinic acid. Without the latter, no significant oxidation of any substrate is observed. Hydroxyl radical formation (Fenton Chemistry) is not considered to be ligand dependent in preceding investigations.
📜 SIMILAR VOLUMES
The selective functionalization of alkane was achieved in a good yield. by a simple Fe"Clz salt and bis(trimethylsily1) peroxide in pyridine. Unlike the Fen-HZ02 system, no extra ligand was needed. The presence of a carbon radical from the Fen-Few manifold was proposed to explain the results.
In the Fem-Fe v manifold the formation of the iron-carbon bond was found to be very fast, but the evolution to give ketone was slow at -20 \*C and -40 \*C. However, the efficiency at the latter temperature was good. The iron-carbon bond can be captured rapidly by I" or by PhSeH. We have confirmed th