Abstract
A number of previously undescribed alkyl-1,3,2-dioxaborinanes were synthesized by condensation of substituted 1,3-diols with alkylboron dichlorides or dibutyl isopropylborate. It was shown by PMR spectroscopy that the 2,5-dialkyl-1,3,2-dioxaborinane molecules are conformationally homogeneous and do not contain an axial substituent in the 5 position, whereas the 2-isopropyl-5,5-dimethyl-1,3,2-dioxaborinane molecules exist in a state of rapid ring inversion, and introduction of methyl substituents in the 4, 4, and 6 positions of the 1,3,2-dioxaborinane ring leads to distortion of the ring conformation and conformational heterogeneity of the investigated sample. The observed regularities are explained from the position of intensive “oxygen-boron” electron exchange in the heteroring. It is concluded that the 2,5-dialkyl-1,3,2-dioxaborinane molecules have primarily a conformation with a semiplanar form.
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Literature cited
A. I. Gren', A. M. Turyanskaya, and A. V. Vaigt, in: Problems in Stereochemistry [in Russian], No. 6, Kiev (1977), p. 87.
A. I. Gren', Doctoral Dissertation, Odessa State University, Odessa (1974).
A. V. Bogat-skii, in: Application of Conformational Analysis in the Synthesis of New Organic Substances [in Russian], Odessa (1975), p. 3.
P. M. Maitlis, Usp. Khim.,33, 748 (1964).
F. Davis, I. Turchi, B. Maryanoff, and R. Hutching, J. Org. Chem.,37, 1583 (1972).
D. Carton, A. Pontier, M. Ponet, J. Soulie, and P. Cadiot, Tetrahedron Lett., No. 28, 2333 (1975).
W. Woods, I. Bengelsdorf, and D. Hunter, J. Org. Chem.,31, 2766 (1966).
W. Woods and P. Strong, J. Am. Chem. Soc.,88, 4667 (1966).
R. Mehrotra and G. Srivastava, J. Indian Chem. Soc.,39, 203 (1962).
R. Cragg and M. Nazery, J. Chem. Soc., Dalton Trans., No. 13, 1438 (1974).
W. Gerrard, Organic Chemistry of Boron, Academic Press (1961),
S. Kuribayashi, Bull. Chem. Soc. Jpn.,46, 1045 (1973).
P. Finocchiaro, D. Gust, and K. Mislow, J. Am. Chem. Soc.,95, 7029 (1973).
T. Urbanski, D. Gürne, R. Kolinski, H. Piotrowska, A. Janczyk, B. Serafin, M. Szretter-Szmid, and M. Witanowski, Nitro Compounds. Proceedings of the International Symposium, Warsaw (1963), p. 195.
W. Whitmore, J. Am. Chem. Soc.,63, 124 (1941).
R. Nystrom and W. Brown, J. Am. Chem. Soc.,69, 1197 (1947).
P. Brindly, W. Gerrard, and M. Lappert, J. Chem. Soc., 2956 (1955).
B. M. Mikhailov and T. A. Shchegoleva, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 9, 1080 (1957).
J. Prichard and R. Vollmer, J. Org. Chem.,28, 1545 (1963).
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See [1] for communication XLVIII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp, 26–30, January, 1978
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Kuznetsov, V.V., Gren', A.I., Bogat-skii, A.V. et al. Stereochemistry of heterocycles. Chem Heterocycl Compd 14, 19–22 (1978). https://doi.org/10.1007/BF00635935
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DOI: https://doi.org/10.1007/BF00635935