A new type of amide formation from thiocarboxylic acid and alkyl azide
β Scribed by Sang-Don Park; Jung-Hee Oh; Dongyeol Lim
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 61 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
We studied the coupling of thiocarboxylic acid and alkyl azide using various triaryl phosphines. Amide formation greater than 95% was achieved when the free-formation of Staudinger intermediate with electron deficient triaryl phosphines was employed.
π SIMILAR VOLUMES
Equimolar amounts of carboxylic acids, aryl or alkyl azides, and Ph3P in refluxing benzene (hexane, toluene) afford amides in good yields. Insolubility of zwitterions Ph3&NH(CH2),COO', arising from w-azido acids and Ph3P, limits the utilization of the method for loctame formation. A plethora of phos
A new method for the formation of amides on solid phase has been developed. The procedure involves the reaction between activated acids in solution and resin bound iminophosphoranes generated from the corresponding azides and tributylphosphine. The method is particularly attractive when starting fro