Thermolysis of bis(diarylmethylenecarbamoyl) peroxides.
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概要
- 論文の詳細を見る
Diacyl peroxides of structure (XC<SUB>6</SUB>H<SUB>4</SUB>)<SUB>2</SUB>C=N–C(=O)OOC(=O)–R (R=(XC<SUB>6</SUB>H<SUB>4</SUB>)<SUB>2</SUB>C=N, X=H (<B>1</B>), X=2-CH<SUB>3</SUB> (<B>3</B>), X=4-CH<SUB>3</SUB>; R=4-ClC<SUB>6</SUB>H<SUB>4</SUB>, X=H (<B>2</B>) have been prepared by the reaction between the corresponding carbamoyl chloride and hydrogen peroxide-urea complex in the presence of pyridine or between the carbamoyl chloride and 4-chloroperbenzoate in anhydrous ether at low temperature. Thermolysis of <B>1</B>–<B>3</B> follows first order kinetics. The large rates of thermolysis of <B>1</B> and <B>3</B> relative to those of bis(diphenylmethyleneacetyl) peroxide have been ascribed to steric compressions of <B>1</B> and <B>3</B> in the ground state and to the concerted cleavage of three bonds. Stable diphenylmethyleneamino radicals do not substitute in toluene by themselves but they do with the aid of aroyloxy radicals. The iminyl radicals abstract hydrogen from the methyl group of toluene, and the rate constant has been estimated to be 5×10<SUP>2</SUP>–2×10<SUP>3</SUP>M<SUP>−1</SUP>s<SUP>−1</SUP> at 50 °C.
- 公益社団法人 日本化学会の論文
著者
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Suehiro Tadashi
Department of Chemistry Faculty of Science The University of Tokyo
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Matsui Yukio
Department of Chemistry, Faculty of Sciences, Gakushuin University
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Inoguchi Yoshio
Department of Chemistry, Faculty of Sciences, Gakushuin University
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