Ta. Vaganova et al., REDUCTIVE ACTIVATION OF ARENES .7. ALKYLATION OF 9-CYCANOANTHRACENE 2-ELECTRON REDUCTION PRODUCTS IN LIQUID-AMMONIA, Tetrahedron, 50(33), 1994, pp. 10011-10020
The reactions of the 9-cyanoanthracene dianion generated by the action
of two equivalents of potassium in liquid ammonia with primary alkyl
iodides and bromides gave 9-cyano-9,10-dialkyl-9,10-dihydroanthracenes
. The alkylation of the 9-cyano-9,10-dihydro-9-anthryl anion generated
by the two-electron reduction of 9-cyanoanthracene in liquid ammonia
in the presence of ammonium chloride gave 9-cyano-9-alkyl-9,10-dihydro
anthracene. The results obtained by using cyclopropylmethyl bromide as
model reagent suggest these reactions to proceed through S-N mechanis
m. The spatial structure of 9,10-dihydroanthracene derivatives obtaine
d is discussed.