Birch

Transformation of aromatic compounds into dihydroaromatics using sodium and alcohol in aqueous ammonia.

Heterocyclic and steroid compounds can react in the same manner.

Benkeser modification - using lithium in aliphatic amines in the presence of alcohols.

Also see Lukes.

Bibliography

• Hückel W. et al., Ann., 1939, 540, 157; 1958, 614, 47; Chem. Ber., 1955, 88, 338; 1956, 89, 150, 481, 2098, 2105.
• Birch A. J. et al., J. Chem. Soc., 1944, 430; 1945, 809; 1956, 593; 1947, 102, 1642; 1949, 2531; 1951, 1945.
• Benkeser R. A., Robinson R. E., Landesman H., J. Am. Chem. Soc., 1952, 74, 5669.
• Benkeser R. A. et al., J. Org. Chem., 1964, 29, 1313.
• Harley R. G., Synthesis, 1970, 2, 161.
• Murai Akio, Arita Keiko, Masamune Tagashi, Bull. Chem. Soc. Japan, 1973, 46, 3536-3544.