ISSN:
0570-0833
Keywords:
Diazo group transfer
;
Diazo compounds
;
Synthetic methods
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
11 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/anie.196707331
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