Conclusions
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1.
By x-ray crystallographic analysis it was confirmed that the product from the methylation of Traube's salt has the methoxyazoxy structure, which is also preserved in the product from its reaction with formaldehyde, i.e., they are in fact bis(methoxy-N,N,O-azoxy)-and bis(methoxy-N,N,0-azoxy)bis(hydroxymethyl)methanes.
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2.
In the investigated compounds the Z form of the planar methoxyazoxy fragments, which form dihedral angles close to right angles with each other, is realized. The CH2O fragments of the hydroxymethyl groups in bis(methoxy-N,N,O-azoxy)bis(hydroxymethyl)methane lie in the plane of the methoxyazoxy groups, although there are no intramolecular hydrogen bonds in the molecule.
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Literature cited
V. N. Yandovskii, B. V. Gidaspov, and I. V. Tselinskii, Usp. Khim.,49, 449 (1980).
V. N. Yandovskii, A. D. Misharov, I. V. Tselinskii, et al., Zh. Org. Khim.,16, 292 (1980).
E. Hickmarm, E. Hâdicke, and W. Reuther, Tetrahedron Lett., 2457 (1979).
E. H. White, M. J. Todd, M. Ribi, et al., Tetrahedron Lett., 4467 (1970).
V. D. Cherepinskii-Malov, A. S. Mukhametzyanov, A. G. Andrianov, and G. A. Marchenko, Zh. Strukt. Khim.,24, 164 (1983).
V. D. Cherepinskii-Malov, G. A. Marchenko, A. S. Mukhametzyanov, and B. I. Buzykin, Izv. Akad. Nauk SSSR, Ser. Khim., 954 (1985).
B. M. Aebischer, H. W. Hanssen, A. T. Vasella, and W. B. Schweizer, J. Chem. Soc., Perkin Trans. I, 2139 (1982).
G. A. Marchenko, A. S. Mukhametzyanov, and I. V. Tselinskii, Zh. Org. Khim.,21, 1428 (1985).
Yu. V. Zefirov and P. M. Zorkii, Zh. Strukt. Khim.,15, 118 (1974).
R. Huber, R. Langer, and W. Hoppe, Acta Crystallogr.,18, 467 (1965).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1777–1781, August, 1987.
The authors express their gratitude to A. S. Mukhametzyanov and L. V. Skvortsova for taking part in the preparation of the samples.
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Marchenko, G.A., Chertanova, L.F., Struchkov, Y.T. et al. Crystal and molecular structure of BIS(Methoxy-N,N,O-azoxy)methane and the product from its reactions with formaldehyde. Russ Chem Bull 36, 1646–1649 (1987). https://doi.org/10.1007/BF00960123
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DOI: https://doi.org/10.1007/BF00960123