The reactions of a variety of diazo compounds with sulfur dioxide in ethanol.

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概要

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• The reactions of several diazomethanes bearing a variety of substituents with sulfur dioxide were carried out in ethanol. The reaction of a diazomethane possessing an electron-releasing group gave the olefin as the major product. On the contrary, the ethyl ethers were predominantly afforded from the reactions of the diazomethanes containing an electron-withdrawing group. Moreover, the ethyl alkanesulfonates were obtained in the cases bearing the substituent of an intermediate electronic character. The observed product distribution is interpreted in terms of the nucleophilicity of the α-carbon atom of the diazomethane: the preference of the formation of sulfene by the electrophilic attack of SO<SUB>2</SUB> on the diazomethane to the acid-catalyzed decomposition by ethyl hydrogen sulfite reflects the nucleophilicity of the α-carbon atom in the diazomethane.

• 公益社団法人 日本化学会の論文

著者

• Nagai Toshikazu

  Institute Of Chemistry College Of General Education Osaka University

• Tanabe Toyoshige

  Institute of Chemistry, College of General Education, Osaka University

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• Stereochemistry in the conversion of phenyldiazomethane into stilbenes and spirooxetanes caused by tetrahalogenated 1,4-benzoquinones. Effects of halogen substituents.
• Products and kinetic substituent effects in the reactions of diaryldiazomethanes with 2,5-dichloro-p-benzoquinone.
• Structural effects in the reactions of diazoalkanes with 2,3-dichloro-5,6-dicyanobenzoquinone.
• Addition of diphenyldiazomethane to unsubstituted and chloro-substituted 1,4-benzoquinones. Effects of chloro substituents on the addition modes.
• Reaction of 9-diazofluorene with 2,3-dichloro-5,6-dicyano-p-benzoquinone: The structure and the behaviors of the resulting product.
• Formations and reactions of cation radicals from compounds possessing a p-dimethylaminophenyl group by reactions with o-sulfobenzoic anhydride.
• Addition of 9-diazofluorene to unsubstituted and chloro-substituted 1,4-benzoquinones. A comparison with the addition of diphenyldiazomethane.
• Synthesis of substituted crown ether acetals.
• Reactions of aryldiazomethanes with chloranil.
• Substituent effects in the acid-catalyzed hydrolysis of cyclic acetals of benzophenones.
• Solvent effects in the conversion of phenyldiazomethane into stilbene and spirooxetane in the reaction with chloranil.
• Polar effects in the reactions of a series of substituted diphenyldiazomethanes with chloranil.
• Kinetic solvent effects in the decomposition of diphenyldiazomethane with chloranil and 2,5-dichloro-p-benzoquinone.
• The reactions of a variety of diazo compounds with sulfur dioxide in ethanol.
• Reactions of a variety of diazoalkanes with o-sulfobenzoic anhydride.
• The reactions of aryldiazomethanes with sulfur dioxide in the presence of enamines.

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