Anion activation in the synthesis of ethers from oxygen anions and p-chloronitrobenzene

C Paradisi, U Quintily, G Scorrano

Index: Paradisi, Cristina; Quintily, Ugo; Scorrano, Gianfranco Journal of Organic Chemistry, 1983 , vol. 48, # 18 p. 3022 - 3026

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Citation Number: 28

Abstract

Reactions of 1-chloro-4-nitrobenzene (1) with alkoxide ions in the parent alcohols do not afford satisfactory yields of the expected alkyl 4-nitroaryl ether except in the case of the short- chain primary alcohols. We report that in the model reaction of 1 with KOH in 2-propanol good yields of 1-isopropoxy-4nitrobenmne (2) are obtained provided BulNBr or alkali ion complexing agents such as 18-crown-6, Carbowax 20M, MPEG 5000, and Triton X-100 ...