BULLETIN OF THE
Article
SNAr Reactions of 1-Halo-2,4-dinitrobenzenes with Alkali-Metal Ethoxides
KOREAN CHEMICAL SOCIETY
C. S. Jeung, J. B. Song, Y. H. Kim, J. Suh, Bioorg. Med. Chem.
Lett. 2001, 11, 3061.
18-Crown-6-ether was recrystallized from acetonitrile and
dried over P2O5 in vacuo. The anhydrous ethanol was further
dried over magnesium and distilled under N2 just before use.
1-Halo-2,4-dinitrobenzenes (6a–6d) and other chemicals
were of the highest quality available.
Kinetics. Kinetic study was performed using a UV–Vis
spectrophotometer equipped with a constant-temperature
circulating bath. The reactions were followed by monitoring
appearance of 1-ethoxy-2,4-dinitrobenzene at 310 nm.
Pseudo-first-order conditions with the EtOM concentration
at least 20 times greater than the substrate concentration were
used. Generally, reactions were followed for 9–10 half-lives
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and kobsd values were calculated using the equation, ln (A∞
–
At) = − kobsdt + C. The kinetic conditions and the kobsd
values are summarized in Tables S1–S8.
Product Analysis. 1-Ethoxy-2,4-dinitrobenzene was formed
quantitatively and identified as one of the products by compar-
ison of the UV–Vis spectrum after completion of the reaction
with that of the authentic sample under the same reaction
condition.
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Acknowledgments. Publication cost of this paper was sup-
ported by the Korean Chemical Society.
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SupportingInformation. Additionalsupportinginformation
is available in the online version of this article.
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Bull. Korean Chem. Soc. 2015, Vol. 36, 1812–1818
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