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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 5, Number 3
March 20, 1984 

Reactions of Aryl Halides with Phenoxides and Alkoxides by Phase Transfer Catalysis
Bong Rae Cho, Sung Dae Park
The reaction of aryl halides with phenoxides and alkoxides were investigated under phase transfer catalytic conditions. 2,4-Dinitro- and 4-nitrohalobenzenes reacted readily with phenoxides in NaOH(aq)-benzene in the presence of Bu4N+Br, affording the products quantitatively. Although the aryl halides did not react with alkoxides under the same condition, the reactions were completed within 2 hours at room temperature when conducted under solid-liquid phase transfenr catalytic condition. The reactivity of aryl halides was in the order, Ar = 2,4-dinitrophenyl > 4-nitrophenyl, and X = F > Cl, consistent with the SNAr mechanism. The reactivity of oxyanions increased with the change of reaction condition from liquid-liquid to solid-liquid phase transfer catalysis. The results were explained with the concentration and the degree of hydration of the anion in benzene.
126 - 129
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