The Journal of Organic Chemistry

Metal-ammonia reduction. VI. Stereospecific alkylation of the 9-alkyl-9, 10-dihydro-10-anthryl carbanion

RG Harvey, CC Davis

Index: Harvey,R.G.; Davis,C.C. Journal of Organic Chemistry, 1969 , vol. 34, # 11 p. 3607 - 3609

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Citation Number: 33

Abstract

cis-9, 1O-Dialkyl-9, lO-dihydroanthracenes are synthesized stereospecifically by addition of an alkyllithium reagent to anthracene in tetrahydrofuran and alkylation with an alkyl halide (method A) or alkylation of 9, lO-dihydroanthracene with n-butyllithium in ether-ammonia and excess alkyl halide (method B). Analogous reactions in the benz [a] anthracene and dibenz [a, h] anthracene series proceed with similar stereospecificity.

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