The Preparation and Reactions of Benzoylnitrile Oxide from Dimethylphenacylsulfonium Bromide

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概要

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• The nitrosation of dimethylphenacylsulfonium bromide (I) with sodium nitrite and hydrochloric acid in water gave 3,4-dibenzoyl-1,2,5-oxadiazole 2-oxide (II) in a 76% yield. The nitrosation of I in a similar manner in 1 : 1 dioxane-water afforded ω-chloro-ω-isonitrosoacetophenone (III) in an 80% yield. The treatment of III with triethylamine produced II through benzoylnitrile oxide (IX). 1,3-Dipolar cycloadditions of IX generated from III were conducted, using methyl methacrylate, styrene, acrylonitrile, and ethyl chloroformate as dipolarophiles, to yield the expected cycloadducts. The mechanisms of these reactions are discussed.

• 公益社団法人 日本化学会の論文

著者

• Otsuji Yoshio

  Department Of Applied Chemistry College Of Engineering University Of Osaka Prefecture

• Imoto Eiji

  Department of Applied Chemistry College of Engineering The University of Osaka Prefecture

• Yoshida Akihiko

  Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture

• Tsujii Yasuhiro

  Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture

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