The selective functionalization of saturated hydrocarbons. Part 43. Modified Gif oxidation in acetonitrile
β Scribed by Derek H.R. Barton; Tingsheng Li
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 406 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
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 isolation of cyclohexanone and cyclohexanol by simple distillation.
π SIMILAR VOLUMES
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 bromination of saturated hydrocarbons was studied in the GoAggln system using CBrCls and other polyhaloalkanes. This bromination reaction was compared to free radical processes by (i) evaluating the rates of reactions for a series of polyhaloalkanes, by (ii) measuring the selectivity of the diff