Influence of the nature of the base electrolyte on the regioselectivity of the cathodic hydrodimerization of 1-acetylnaphthalene in an aprotic medium

Influence of the nature of the base electrolyte on the regioselectivity of the cathodic hydrodimerization of 1-acetylnaphthalene in an aprotic medium Full article

Journal

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science
ISSN: 2376-8444 , E-ISSN: 0568-5230

Output data

Year: 1991, Volume: 40, Number: 2, Pages: 372-375 Pages count : 4 DOI: 10.1007/bf00965434

Authors

Gul'tyai V.P. ¹ , Rubinskaya T.Ya. ¹ , Mendkovich A.S. ¹

Affiliations

1	N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

The electrolysis of 1-acetylnaphthalene at a controlled potential [DMF, Ba· (CIO4)2] leads to the formation of 5-acetyl-1,2,4,5-tetrahydro-2-methyl-2-(1-naphthyl)-1, 4-methano-3-benzoxepine (yield of 60%); this is explained by the stabilization of the dimeric dianion of the “head-tail” type by the Ba2+ cations. The formation of 2,3-dimethyl-2,3-di-(1-naphthyl)-butane-2,3-diol is observed with the acylotropic rearrangement of the intermediate anion, leading to 2-acetylnaphthalene, in the presence of lithium cations.

Gul'tyai V.P. , Rubinskaya T.Y. , Mendkovich A.S.
Influence of the nature of the base electrolyte on the regioselectivity of the cathodic hydrodimerization of 1-acetylnaphthalene in an aprotic medium
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1991. V.40. N2. P.372-375. DOI: 10.1007/bf00965434 OpenAlex

OpenAlex:

W2088869669

DB	Citing
OpenAlex	3