Journal of Organic Chemistry p. 3602 - 3605 (1989)
Update date:2022-08-11
Topics:
Marcinow, Zbigniew
Hull, C. Eugene
Rabideau, Peter W.
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.
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Doi:10.1016/0304-5102(89)85001-1
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