EXPERIMENTAL AND QUANTUM-CHEMICAL STUDY OF THE REACTIONS OF 1,10-ANTHRAQUINONES WITH ALCOHOLS AND AMINES

EXPERIMENTAL AND QUANTUM-CHEMICAL STUDY OF THE REACTIONS OF 1,10-ANTHRAQUINONES WITH ALCOHOLS AND AMINES Full article

Journal

Tetrahedron
ISSN: 0040-4020

Output data

Year: 1995, Volume: 51, Number: 10, Pages: 3061-3076 Pages count : 16 DOI: 10.1016/0040-4020(95)00046-B

Authors

Gritsan N.P. ¹ , Klimenko L.S. ² , Leonenko Z.V. ¹ , Mainagashev I.Ya. ² , Mamatyuk V.I. ² , Vetchinov V.P. ²

Affiliations

1	Institute of Chemical Kinetics and Combustion and Novosibirsk State University, 630090, Novosibirsk, Russia
2	Institute of Organic Chemistry, 630090, Novosibirsk, Russia

The primary stage of the reaction between 9-aryloxy-1,10-anthraquinones and methanol is the nucleophilic 1,4-addition which gives rise to the adduct, corresponding to 1-hydroxy-9-methoxy-9-aryloxy-10-anthrone. The reaction of 9-aryloxy-1,10-anthraquinones with the primary aliphatic and aromatic amines results in the formation of 9-alkyl(aryl)aminol-1,10-anthraquinones that are in a tautomeric equilibrium with 1-hydroxy-9,10-anthraquinone-9-alkyl(aryl)imines. The quantum chemical calculations of the enthalpy of 9-amine-1,10-anthraquinone isomerization are in agreement with the experimentally recorded influence on the tautomeric equilibrium of the nature of amine, solvent, and substituent in the anthraquinone nucleus. The data of quantum chemical calculations confirm the addition-elimination mechanism of the reaction of 1,10-anthraquinones with amines.

Gritsan N.P. , Klimenko L.S. , Leonenko Z.V. , Mainagashev I.Y. , Mamatyuk V.I. , Vetchinov V.P.
EXPERIMENTAL AND QUANTUM-CHEMICAL STUDY OF THE REACTIONS OF 1,10-ANTHRAQUINONES WITH ALCOHOLS AND AMINES
Tetrahedron. 1995. V.51. N10. P.3061-3076. DOI: 10.1016/0040-4020(95)00046-B WOS Scopus

Published print:

Mar 1, 1995

Web of science	WOS:A1995QL65700020
Scopus	2-s2.0-0028815511
OpenAlex	W2013068984