The selective functionalization of saturated hydrocarbons. Part 46. An investigation of Udenfriend's system under Gif conditions
β Scribed by Derek H.R. Barton; Nathalie C. Delanghe
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 257 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0040-4020
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π SIMILAR VOLUMES
The role ofpyridine and of many substituted pyridines in Gif oxidation chemistry has been examined. In the presence of a suitable pyddine type base most of the solvent can be replaced by acetonitrile without diminishing the yield of oxidation products. The use of 4-tert-butylpyridine permits the iso
The stereoselectivity of various Gif-type reactions was evaluated using trans-l,4-dimethylcyclohexane as a chemical probe. The results revealed that these reactions were moderately stereoselective. The outcome of the reactions was preferentially formed in the more stable equatorial configuration.
The Gif system for selective hydrocarbon oxidation can be carried out replacing the zinc by a cathodic electrochemical reduction: the yields obtained and the selectivities observed are very similar.
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.