Dutt–Wormall疊氮化反應

芳胺重氮化后，接著再和磺酰胺（如TsNH2，MsNH2）反應，水解得到芳基疊氮的反應。此反應最早由Dutt, Whitehead和Wormall在1921年報道。芳基重氮鹽和磺酰胺反應先得到磺酰基芳基疊氮，水解后得到產物。類似的疊氮化合物也可以通過重氮鹽和氨，肼和羥胺反應制得。

反應機理

反應實例

Phenylazide (4). 1 (4.6 g, 50 mmol) in 25 mL H2O and 35% HCl (15 mL) was diazotized with aq NaNO2 (3.5 g, 55 mmol). After diazotization (starch-iodine paper), p-toluenesulfonamide 3 (8.5 g, 50 mmol) in water (175 mL) and NaOH (6 g, 150 mmol) were added. After 10–15 min, filtration afforded 8 g of 4 (85%), mp 85 C.

【Dutt PK, Wormall A， J Chem Soc， 1921， 119， 2088】

相關文獻

1 Dutt PK, Wormall A J Chem Soc 1921 119 2088

2 Dutt PK J Chem Soc 1924 125 1463

3 Bretschnelder H Monatsh 1950 81 970

4 Hassner A Angew Chem Int 1986 25 478

5 Bols M J Org Chem 2003 68 9453

6 Zimmermann V Angew Chem Int 2005 44 5188

參考資料

一、Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 134。

二、Comprehensive Organic Name Reactions and Reagents，946-948.