New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups

M. Regitz

doi:10.1002/anie.196707331

New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups

DOI Web Site Web Site 被引用文献11件

M. Regitz

書誌事項

公開日: 1967-09

権利情報

http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/anie.196707331

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>When an arenesulfonyl azide, particularly <jats:italic>p</jats:italic>‐toluenesulfonyl azide, reacts, in the presence of a base, with a compound containing an active methylene group, the two hydrogen atoms of the active methylene group are replaced by a diazo group to form a diazo compound and an arenesulfonamide. The method may be used for the synthesis of the diazo derivatives of cyclopentadienes, cyclohexadienes, 1,3‐dicarbonyl, 1,3‐disulfonyl, and 1,3‐ketosulfonyl compounds, ketones, carbonic acid esters, and β‐iminoketones. Secondary reactions can lead to azo compounds and heterocycles such as 1,2,3‐triazoles, 1,2,3‐thiadiazoles, and pyrazolin‐4‐ones. Azidinium salts react in the same way, but in this case an acidic reaction medium is necessary, a fact that is sometimes advantageous.</jats:p>