Conclusions
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1.
When 1,1′-di(3,4-dimethoxyphenyl) diethyl ether (I) is nitrated in ether the NO2 group enters the 6 position of the aromatic rings.
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2.
Together with aromatic substitution, cleavage of the benzyl ether linkage occurs when (I) is nitrated in CCl4, with the formation of benzyl alcohol and nitro ester groups, electrophilic replacement of the side chain by the NO2 groups, and also the formation of the corresponding biphenyl nitro derivative.
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L. L. Sergeeva and N. N. Shorygina, Izv. Akad. Nauk SSSR, Ser. Khim., 1630 (1965).
M. Balfe, A. Evans, J. Kenyon, and K. Nandi, J. Chem. Soc., 803 (1946); B. O. Lindgren, Acta Chem. Scand.,4, 1365 (1950).
L. L. Sergeeva, N. N. Shorygina, and B. V. Lopatin, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1296 (1962).
S. Heden and B. Holmberg, Svensk. Kem. Tidskr.,48, 207 (1936).
V. V. Elkin and N. N. Shorygina, Izv. Akad. Nauk SSSR, Ser. Khim., 1114 (1970).
B. O. Lindgren, Acta Chem. Scand.,4, 1365 (1950).
I. Puskas and E. K. Fields, J. Org. Chem.,31, 4204 (1966).
I. Puskas and E. K. Fields, J. Org. Chem.,32, 3924 (1967).
P. C. Roberti, P. F. York, and W. S. MacGregor, J. Am. Chem. Soc.,72, 5760 (1950).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 924–929, April, 1972.
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Sergeeva, L.L., Shorygina, N.N. Behavior of dibenzyl ether linkage in model lignin compounds during nitration. Russ Chem Bull 21, 875–879 (1972). https://doi.org/10.1007/BF00854491
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DOI: https://doi.org/10.1007/BF00854491