Heterocyclic diazo compounds. 5. Reaction of benzimidazole-2-diazonium salts with naphthols and their ethers
Rent the article at a discountRent now
* Final gross prices may vary according to local VAT.Get Access
The principal pathways for the reaction of benzimidazole-2-diazonium ion salts with naphthols and their methyl ethers in a mixture of phosphoric acid annd acetic acid have been elucidated. In concentrated acidic media, in addition to substitution at the 4-position in naphthol and its ether, azo coupling at the 8-positin is also possible. It has been found that a 2-methoxy group in naphtylazobenzimidazole exhibits anomalously high reactivity with respect to hydrolytic cleavage, which explains the observed ease of dealkylation of the azo compound during the course of the azo coupling sequence.
For Communication No. 4, see .
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 67–72, January, 1992.
S. N. Kolodyazhnaya, L. N. Divaeva, R. A. Sogomonova, and A. M. Simonov, Khim. Geterotsikl. Soedin., No. 5, 637 (1990).
S. N. Kolodyazhnaya, A. M. Simonov, and L. N. Podladchikova, Khim. Geterotsikl. Soedin., No. 6, 829 (1975).
T. I. Godovikova, O. A. Rakitin, and L. I. Khmel'nitskii, Usp. Khim., 52, 777 (1983).
L. S. Efros and M. V. Gorelik, Chemistry and Technology of Intermediates [in Russian], Khimiya, Moscow (1977), p. 432.
K. Venkataraman (ed.) Analytical Chemistry of Synthetic Dyes, Khimiya, Leningrad (1977).
L. A. Fedorov, NMR Spectroscopy of Organic Analytical Reagents and Their Complexes with Metal Ions [in Russian], Nauka, Moscow (1987).
H. Mustroph and R. Bartel, J. Prakt. Chem., 324, 743 (1982).
J. Kelemen, S. Moss, H. Sauter, and T. Wenkler, Dyes and Pigments, No. 3, 27 (1982).
L. Bellamy, Infrared Spectra of Molecules [Russian translation], Inostr. Lit., Moscow (1957).
Y. Kikugava, Synthesis, 124 (1981).
- Heterocyclic diazo compounds. 5. Reaction of benzimidazole-2-diazonium salts with naphthols and their ethers
Chemistry of Heterocyclic Compounds
Volume 28, Issue 1 , pp 58-63
- Cover Date
- Print ISSN
- Online ISSN
- Kluwer Academic Publishers-Plenum Publishers
- Additional Links