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The functionalization of saturated hydrocarbons. Part 23. Gif-type bromination and chlorination of saturated hydrocarbons: a non-radical reaction

✍ Scribed by Derek H.R. Barton; Éva Csuhai; Darío Doller

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
863 KB
Volume
48
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 different systems towards various saturated hydrocarbons and by (iii) analyzing the product distribution arising from the bromination of cyclohexyl bromide under both the GoAggn* type conditions and from known processes for alkyl radical generation. Some chlorine containing reagents were also examined for C-Cl bond formation in the GoAggnl system. All the experimental findings support a mechanism for the reaction that is different from one involving free radicals. This non-radical pathway is common in all Gif-type systems, as seen in common patterns of selectivity.

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The selective functionalization of satur
The selective functionalization of saturated hydrocarbons. Part 36. Stereoselectivity studies of Gif-type reactions
✍ Derek H.R. Barton; Warinthorn Chavasiri 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 352 KB

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.