37934-99-9Relevant articles and documents
Efficient Transfer of Chelating Amides into Different Types of Esters and Lactones
Jakob, Uwe,Mundinger, Stephan,Bannwarth, Willi
, p. 6963 - 6974 (2016/02/18)
We describe a general and versatile approach for the conversion of carboxylic acid amides into their corresponding esters despite the fact that the former are thermodynamically more stable. The transformations are mediated by the coordination of CuI by a chelating entity. The resulting weakening of the amide bond allows for nucleophilic attack by alcoholic hydroxyl functions. The principle is demonstrated for a wide variety of transformations, leading to different kinds of esters and lactones. Due to their high resonance energy, amides are generally very stable towards solvolysis. However, bispicolylamides can be activated for alcoholysis by an unusual metal coordination involving the electron pair of the amide nitrogen. Herein, we widened the scope of the reaction by transforming the amides into a range of esters and lactones.
Platinum on carbon-catalyzed precise reduction control of trichloromethyl to Geminal-dichloromethyl groups
Imanishi, Takahiro,Fujiwara, Yuta,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
supporting information; experimental part, p. 771 - 776 (2012/06/30)
Geminal-dichloromethyl derivatives could be efficiently synthesized by the highly chemoselective platinum on carbon-catalyzed mono-dechlorination of trichloromethyl substrates in dimethylacetamide (DMA) as a specific solvent at 25 °C under a hydrogen atmosphere. Copyright
Copper(I)-promoted dechlorinative Surzur-Tanner rearrangement of 2,2,2-trichloroethyl carboxylates
Ram, Ram N.,Meher, Nabin Kumar
, p. 145 - 147 (2007/10/03)
(Matrix presented) 2,2,2-Trichloroethyl carboxylates undergo highly efficient dechlorinative Surzur-Tanner rearrangement with 2 equiv of a 1:1 molar mixture of CuCl and bpy in boiling DCE to give 1-chloroethenyl carboxylates in which copper appears to play an important role, probably by coordinating the initial radical or as a Lewis acid catalyst.