METAL-AMMONIA REDUCTION .6. STEREOSPECIFIC ALKYLATION OF 9-ALKYL-9,10-DIHYDRO-10-ANTHRYL CARBANION

cis-9,10-Dialkyl-9,10-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 9,10-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. © 1969, American Chemical Society. All rights reserved.