REDUCTIVE ACTIVATION OF ARENES .7. ALKYLATION OF 9-CYCANOANTHRACENE 2-ELECTRON REDUCTION PRODUCTS IN LIQUID-AMMONIA

REDUCTIVE ACTIVATION OF ARENES .7. ALKYLATION OF 9-CYCANOANTHRACENE 2-ELECTRON REDUCTION PRODUCTS IN LIQUID-AMMONIA Full article

Journal

Tetrahedron
ISSN: 0040-4020

Output data

Year: 1994, Volume: 50, Number: 33, Pages: 10011-10020 Pages count : 10 DOI: 10.1016/S0040-4020(01)89616-2

Authors

Vaganova T.A. ¹ , Panteleeva E.V. ¹ , Tananakin A.P. ¹ , Shteingarts V.D. ¹ , Bilkis I.I. ²

Affiliations

1	Institute of Organic Chemistry, Siberian Division of the Russian Academy of Sciences, Novosibirsk, 630090, Russia
2	The Hebrew University of Jerusalem, Faculty of Agriculture, P.O.Box 12. Rehovot 76-100, Israel.

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 S-N mechanism. The spatial structure of 9,10-dihydroanthracene derivatives obtained is discussed.

Vaganova T.A. , Panteleeva E.V. , Tananakin A.P. , Shteingarts V.D. , Bilkis I.I.
REDUCTIVE ACTIVATION OF ARENES .7. ALKYLATION OF 9-CYCANOANTHRACENE 2-ELECTRON REDUCTION PRODUCTS IN LIQUID-AMMONIA
Tetrahedron. 1994. V.50. N33. P.10011-10020. DOI: 10.1016/S0040-4020(01)89616-2 WOS Scopus OpenAlex

Published print:

Jan 1, 1994

Web of science:	WOS:A1994PC67600016
Scopus:	2-s2.0-0028029240
OpenAlex:	W1980939198

DB	Citing
Web of science	10
Scopus	9
OpenAlex	7