Abstract
X-Ray structural analysis has been used to establish the structures of the heterocyclic oxidation products of N-arylthioureas. The oxidation product of N,N'-diphenylthiourea (Hugershoff 's base) is 2-[N-phenyl-N-(phenylamino-phenylimino-methyl)] aminobenzothiazole. The oxidation product of N-phenylthiorea (Hector's base) has been confirmed to be 5-imino-4-phenyl-3-phenylamino-4H-1,2,4-thiodiazoline. The acetyl group in its acetyl derivative has been shown to be attached to the imine nitrogen atom.
Similar content being viewed by others
Literature cited
D. S. Hector, Ber., 22, 1176 (1889).
A. Hugershoff, Ber., 36, 3121 (1903).
K. Dost, Ber., 39, 863 (1906).
L. L. Bambas, Five-Membered Hetrocycllc Compounds, Wiley-Interscience, New York (1952), p. 35.
W. A. Sherman, Heteroycyl. Compd., 7, 558 (1961).
F. Kurzer, Adv. Heterocycl. Chem., 5, 126 (1965).
C. Christophersen, T. Ottersen, K. Seff, and S. Treppendahl, J. Am. Chem. Soc., 97, 5237 (1975).
T. Kinoshita, S. Sato, and C. Tamura, Bull. Chem. Soc. Jpn., 49, 2236 (1976).
A. R. Butler, C. Glldewell, and D. C. Liles, Acta Crystallogr., B34, 3241 (1978).
L. V. Yashkina, B. V. Kopylova, I. O. Bragina, I. I. Kandror, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 49, 2306 (1984).
D. S. Hector, Ber., 23, 357 (1890).
K. S. Suresh and C. N. R. Rao, J. Indian Chem. Soc., 37, 581 (1960).
V. K. Verma and K. M. Sarkar, J, Sci. Ind. Res., Sect. B, 21, 238 (1962).
A. Kaiman and L. Parkanyi, Acta Crystallogr., B36, 2372 (1980).
A. Cuthbertson and C. Glidwell, Acta Crystallogr., B37, 1419 (1981).
M. Fehlmann, Acta Crystallogr., B26, 1736 (1970).
P. J. Wheatley, J. Chem. Soc., No. 9, 3636 (1982).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 206–210, February, 1985.
Rights and permissions
About this article
Cite this article
Kandror, I.I., Bel'skii, V.K., Kopylova, B.V. et al. Structure of Hugershoff's and Hector's bases, and acetylated Hector's base. Chem Heterocycl Compd 21, 169–172 (1985). https://doi.org/10.1007/BF00504202
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00504202