Structural effects in the reactions of diazoalkanes with 2,3-dichloro-5,6-dicyanobenzoquinone.
スポンサーリンク
概要
- 論文の詳細を見る
2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) reacted with diazoethane to give stereoisomeric bicyclic diones (<B>3</B>, isomer ratio=3.4) arising from dipolar addition to the C=C bond of DDQ. DDQ reacted with phenyldiazomethane to afford also stereoisomeric bicyclic diones (<B>7</B>) in the ratio of 5:1, together with stilbenes (<B>8</B>). On the other hand, DDQ gave the (ethenyloxy)benzene derivative (<B>14</B>) with 1-phenyldiazoethane. The formation of <B>8</B> and <B>14</B> was interpreted by considering the participation of 1:1 betaines resulting from addition to the C=O bond. The added methanol captures the betaines, thus giving rise to dimethyl acetals of benzaldehyde and acetophenone, along with 2,3-dichloro-5,6-dicyanohydroquinone. These reactivities of DDQ were discussed in comparison with those of chloranil.
- 公益社団法人 日本化学会の論文
著者
-
Oshima Takumi
Institute Of Chemistry College Of General Education Osaka University
-
Nagai Toshikazu
Institute Of Chemistry College Of General Education Osaka University
関連論文
- Hydrogenolysis of gem-Diphenylcyclopropanes Fused with Trihalogenated Quinones
- Trinuoromethyl-substituted Norbornadiene, Useful Solar Energy Material
- Substituent and solvent effects in the reactions of diaryldiazomethanes with 2,3-dichloro-5,6-dicyanobenzoquinone.
- 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.