New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups
Abstract When an arenesulfonyl azide, particularly p ‐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. T...
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crwiley:10.1002/anie.196707331 2024-09-15T18:01:37+00:00 New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups Regitz, M. 1967 http://dx.doi.org/10.1002/anie.196707331 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.196707331 https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.196707331 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Angewandte Chemie International Edition in English volume 6, issue 9, page 733-749 ISSN 0570-0833 journal-article 1967 crwiley https://doi.org/10.1002/anie.196707331 2024-09-05T05:10:13Z Abstract When an arenesulfonyl azide, particularly p ‐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. Article in Journal/Newspaper Carbonic acid Wiley Online Library Angewandte Chemie International Edition in English 6 9 733 749 |
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English |
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Abstract When an arenesulfonyl azide, particularly p ‐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. |
format |
Article in Journal/Newspaper |
author |
Regitz, M. |
spellingShingle |
Regitz, M. New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups |
author_facet |
Regitz, M. |
author_sort |
Regitz, M. |
title |
New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups |
title_short |
New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups |
title_full |
New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups |
title_fullStr |
New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups |
title_full_unstemmed |
New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups |
title_sort |
new methods of preparative organic chemistry. transfer of diazo groups |
publisher |
Wiley |
publishDate |
1967 |
url |
http://dx.doi.org/10.1002/anie.196707331 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.196707331 https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.196707331 |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
Angewandte Chemie International Edition in English volume 6, issue 9, page 733-749 ISSN 0570-0833 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/anie.196707331 |
container_title |
Angewandte Chemie International Edition in English |
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6 |
container_issue |
9 |
container_start_page |
733 |
op_container_end_page |
749 |
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1810438731759353856 |