Metal-ammonia reduction. 15. Regioselectivity of reduction and reductive methylation in the fluorene series

RG Harvey, PP Fu, PW Rabideau

Index: Harvey,R.G. et al. Journal of Organic Chemistry, 1976 , vol. 41, # 16 p. 2706 - 2710

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Citation Number: 14

Abstract

Results Interaction of lithium metal with fluorene in liquid ammonia following the general technique developed earlier1, 8 furnished two dihydro derivatives (2, 3) along with tetrahydrofluorene and recovered fluorene. Product ratios were determined by GLC analysis and found to be markedly dependent upon reaction conditions (Table I). Reaction for 5 min at-78" C quenched with NH4Cl and worked up rapidly by extraction with ether afforded 2 ( ...