Stereochemistry Kolbe reaction

Orientation effects by the electrode surface have been invoked in a large number of other cases (for reviews of the stereochemistry of electrode processes, see Eberson and Homer, 1973 Fry, 1972a), for example in halide reduction (for a review, see Casanova and Eberson, 1973), formation of dimers in the Kolbe reaction (Hawkes et al., 1973), reduction of systems with double and triple bonds (Horner and Roder, 1969), and anodic coupling of 1-methylcorypalline... 

Utley JHP, Yates GB (1978) Electro-organic reactions. Part 11. Mechanism of the kolbe reaction the stereochemistry of reaction of anodically generated cyclohex-2-enyl radicals and cations. J Chem Soc, Perkin Trans II 395-400... 

The classic Kolbe synthesis has been used in recent years in an elegant manner by Schaeffer to prepare a number of natural materials such as the beetle pheromone, 88 ( fO). In a two-electron reaction which takes place through a rearrangement as shown in Fig. 7, 8 was converted to 3 which was used for the synthesis of several interesting cyclopentanoid natural products (fjl). A similar two-electron reaction not involving a rearrangement, led from to 5 ( 8). No stereochemistry is implied in and 5. 

---