115584-24-2Relevant academic research and scientific papers
RADICAL-ANIONS OF AROMATIC COMPOUNDS. XIV. REACTION OF 1-NAPHTHONITRILE RADICAL-ANION WITH ALKYLATING REAGENTS IN LIQUID AMMONIA
Bil'kis, I. I.,Vaganova, T. A.,Shteingarts, V. D.
, p. 1765 - 1770 (2007/10/02)
The main products from the reaction of the 1-naphthonitrile radical-anion with primary alkyl halides in a liquid ammonia-THF medium are the corresponding 1-alkylnaphthalenes.Their formation is due to the extent of 85-90percent to the entry of the alkyl fragment at the ipso position in relation to the cyano group.For the case of the reaction with 4-methoxyphenyltrimethylammonium perchlorate it was shown that the formation of the alkylnaphthalenes is most probably due to the display of nucleophilic characteristics by the 1-naphthonitrile radical-anion.
AROMATIC RADICAL-ANIONS. XI. THE REACTION OF THE PRODUCTS OF THE REDUCTION OF 1-NAPHTHONITRILE BY POTASSIUM IN THF WITH METHYL IODIDE AND WATER
Bil'kis, I. I.,Baganova, T. A.,Denisov, A. Yu.,Shteingarts, V. D.
, p. 1823 - 1829 (2007/10/02)
The action of oxygen on the product of the one-electron reduction of 1-naphthonitrile by potassium in THF gives the starting nitrile an 4,4'-dicyano-1,1'-dinaphthyl, which indicates a reversible dimerization of the 1-naphthonitrile radical-anion.In accord with this conclusions, hydrolysis of these reduction product gives napthalene , 4,4'-dicyano-1,1'-dinaphthyl, 4-cyano-1,1'-dinaphthyl, while the action of CH3I gives 1-methylnapthalene, 1-cyano-1-methyl-1,2-dihydronaphthalene, and 4-cyano-4'-methyl-1,1'-dinaphtyl.
