1. A Birch reduction of naphthalene takes 5 minutes elution time. 2. Of continuing value is the sodium metal mediated Birch reduction of arenes. 3. A common use of sodium dissolved in liquid ammonia is the Birch reduction . 4. Examples include the Pummerer rearrangement, the Pinnick oxidation and the Birch reduction . 5. The mechanism of the Birch reduction has been the subject of much discussion. 6. The Birch Reduction enables the modification of steroids. 7. In the Birch reduction , the secondary reaction is proton abstraction from an alcohol. 8. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol. 9. Cyclohexadienes, many derived from Birch reduction of aromatic compounds, form derivatives ( diene ) Fe ( CO ) 3. 10. Nanotubes can also be alkylated with alkyl halides using lithium or sodium metal and liquid ammonia ( Birch reduction conditions ).