TY - JOUR
T1 - Reductive activation of arenes. VII. Alkylation of 9-cyanoanthracene two-electron reduction products in liquid ammonia.
AU - Vaganova, Tamara A.
AU - Panteleeva, Elena V.
AU - Tananakin, Andrej P.
AU - Shteingarts, Vitalij D.
AU - Bilkis, Itzhak I.
PY - 1994
Y1 - 1994
N2 - 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-dihydroanthracene. The results obtained by using cyclopropylmethyl bromide as model reagent suggest these reactions to proceed through SN mechanism. The spatial structure of 9,10-dihydroanthracene derivatives obtained is discussed.
AB - 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-dihydroanthracene. The results obtained by using cyclopropylmethyl bromide as model reagent suggest these reactions to proceed through SN mechanism. The spatial structure of 9,10-dihydroanthracene derivatives obtained is discussed.
UR - http://www.scopus.com/inward/record.url?scp=0028029240&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)89616-2
DO - 10.1016/S0040-4020(01)89616-2
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AN - SCOPUS:0028029240
SN - 0040-4020
VL - 50
SP - 10011
EP - 10020
JO - Tetrahedron
JF - Tetrahedron
IS - 33
ER -