Competition between Birch Reduction and Bond Cleavage in 1,2-Bis(4-methyl-1-naphthyl)ethane

Article abstract of DOI:10.1021/jo00276a020

The reaction of 1,2-bis(4-methyl-1-naphthyl)ethane with Li, Na, and K in ammonia, THF, and HMPA, or mixtures thereof, has been examined with respect to the factors favoring Birch reduction of the aromatic ring and cleavage of the ethane carbon-carbon bond.Bond cleavage was found to increase relative to ring reduction in the series Li < Na < K and with the solvents NH3 < THF < HMPA.However, the latter position of ammonia may be due to the necessarily restricted low-reaction temperature since only ring reduction was observed at temperatures at or below the boiling pointof ammonia (-33 deg C).A number of reduction and cleavage products were isolated and identified, and the mechanistic pathways for their formation is discussed.