Epoxide opening, Birch conditions, radical

Before turning to epoxide opening with low valent metal complexes, the reduction of epoxides under Birch conditions [10-13] will be discussed very briefly for historical reasons. The initially formed radical is reduced further to give carbanionic species, that do not display the reactivity of radicals. No C - C bond-forming reactions have initially been reported. 

Epoxide Opening by Single Electron Transfer Birch Conditions and Radical Anions... 

In the light of the success of the Birch conditions for reducing organic compounds it is not surprising that epoxides can be opened by solvated electrons [6-9]. The initially formed radical is then further reduced to give carbanionic species, which do not display the reactivity of radicals. This concept has been extended by Bartmann [10], Cohen et al. [11], Conrow [12], and Yus et al. [13,14] who employed aromatic radical anions as the reduc-... 

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