Alkylation of ketoxime with dichloromethane using bases under phase-transfer conditions. Formation of methylene dioxime and novel heteromacrocyclic compounds.

T Hosokawa, T Ohta, Y Okamoto…

Index: Hosokawa, Takahiro; Ohta, Toshiyuki; Okamoto, Yoshihiro; Murahashi, Shun-Ichi Bulletin of the Chemical Society of Japan, 1985 , vol. 58, # 1 p. 194 - 200

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Citation Number: 9

Abstract

Ketoximes, when treated with KO 2 (1 equiv) in the presence of di-μ-chlorobis (2-methylallyl) dipalladium (II)(0.1 equiv per Pd) in dichloromethane, give methylene dioximes in moderate yields. This alkylation of ketoximes with CH 2 Cl 2 is also promoted by the use of potassium carbonate in the presence of phase-transfer catalysts such as 18-crown-6. Study on the reactivity of a series of ketoximes in these reactions shows that proton abstraction by base ...

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