Abstract
Under the conditions of the Fischer reaction, O-phenylhydroxylamine forms mixtures of isomeric (with respect to substitution in the 2 and 3 positions) benzofurans with methyl ketones. Only 3-substituted 2-methylbenzofurans were isolated when methyl ketones with a “strongly activated” methylene group were used as the carbonyl component.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
I. I. Grandberg and N. M. Przheval'skii, Izv. Moskovsk. Sel'skokhoz, Akad. im. K. A. Timiryazeva, 192 (1972).
I. I. Grandberg and T. I. Zuyanova, Khim. Geterotsikl. Soedin., 875 (1968).
B. Robinson, Chem. Rev., 63, 373 (1963).
M. H. Palmer and P. S. McIntyre, J. Chem. Soc., B, No. 4, 446 (1969).
T. Sheradsky, Tet. Letters, 5225 (1966).
D. Kaminsky, I. Shavel, and R. I. Meltzer, Tet. Letters, 859 (1967).
T. Sheradsky, J. Heterocycl. Chem., 4, 413 (1967).
A. Mooradian and P. E. Dupont, J. Heterocycl. Chem., 4, 441 (1967).
A. Mooradin, Tet. Letters, 407 (1967).
L. A. Aksanova, L. M. Sharkova, I. F. Kucherova, and V. A. Zagorevskii, Khim. Geterotsikl. Soedin., 1581 (1970).
K. Nakanishi, Infrared Spectra and Structure of Organic Compounds [Russian translation], Mir, Moscow (1965), p. 64.
K. H. Pausacker and C. I. Schubert, J. Chem. Soc., 814 (1950).
H. Becker, Introduction to the Electronic Theory of Organic Reactions [Russian translation], Mir, Moscow (1965), p. 198.
C. L. Bumgardner and R. L. Lilly, Chem. Ind., 539 (1962).
Author information
Authors and Affiliations
Additional information
See [1] for communication XXXIII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 31–36, January, 1973.
Rights and permissions
About this article
Cite this article
Grandberg, I.I., Sorokin, V.I. Indoles. Chem Heterocycl Compd 9, 26–30 (1973). https://doi.org/10.1007/BF00476142
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00476142