The Benkeser reduction reaction is the catalytic hydrogenation of polycyclic aromatic hydrocarbons, especially naphthalene using lithium or calcium metal and any of the following primary amines or low molecular weight alkyl groups as reductants: -CH3, -CH2CH3, -CH2CH2CH3, -CH2CH2NH2.
This reaction is a modification of the Birch reduction.[1]
Its products include bicyclo[3.3.0]dec-(1,9)-ene, bicyclo[3.3.0]dec-(1,2)-ene and bicyclo[3.3.0]decane.[2]