The result of this reaction differs from transition metal hydrogenations by not proceeding all the way to cyclohexane rings.
Its namesake discovered it in 1944 by building on the work of Wooster and Godfrey. Calculations demonstrated that, contrary to the suggestion of this reaction's discoverer, initial protonation in the presence of an electron donor occurs at the ortho position. A modification which involves polycyclic hydrocarbons like naphthalene is called the Benkeser reaction. The mechanism of this reaction depends on the presence of solvated electrons from an electride salt. The result of this reaction differs from transition metal hydrogenations by not proceeding all the way to cyclohexane rings. A. L. Wilds noted that it works better with lithium and t-butyl alcohol, though it was first accomplished with sodium and ethanol. Occurring in a solution of alcohol, a salt, and ammonia, for 10 points, name this reaction that converts aromatic rings to 1,4 cyclohexadienes.
Its namesake discovered it in 1944 by building on the work of Wooster and Godfrey.
Birch Reduction