Competition between Birch reduction and bond cleavage in 1, 2-bis (4-methyl-1-naphthyl) ethane

Z Marcinow, CE Hull, PW Rabideau

Index: Marcinow, Zbigniew; Hull, C. Eugene; Rabideau, Peter W. Journal of Organic Chemistry, 1989 , vol. 54, # 15 p. 3602 - 3605

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Citation Number: 2

Abstract

The reaction of 1, 2-bis (4-methyl-l-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 ...