21151-56-4Relevant articles and documents
Silver-catalyzed decarboxylative chlorination of aliphatic carboxylic acids
Wang, Zhentao,Zhu, Lin,Yin, Feng,Su, Zhongquan,Li, Zhaodong,Li, Chaozhong
experimental part, p. 4258 - 4263 (2012/04/10)
Decarboxylative halogenation of carboxylic acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic carboxylic acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic carboxylic acids. Thus, with the catalysis of Ag(Phen)2OTf, the reactions of carboxylic acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.
Decarboxylation Rates of Benzoyloxyl Radicals as Determined by Laser Flash Photolysis. Further Insight into the Mechanism for Photodecomposition of Dibenzoyl Peroxides
Misawa, Hiroaki,Sawabe, Ken,Takahara, Shigeru,Sakuragi, Hirochika,Tokumaru, Katsumi
, p. 357 - 360 (2007/10/02)
Bis(4-methoxybenzoyl), bis(4-chlorobenzoyl), and dibenzoyl peroxide were photolyzed in various solvents by 308-nm laser pulses to determine the rate constants for decarboxylation of the corresponding benzoyloxyl radicals.The activation energies of this pr
benzenes
Menkisoglou-Spyroudi, Ourania,Varvoglis, Anastasios
, p. 795 - 798 (2007/10/02)
The title compounds (3) have been prepared and their chemical properties studied.With iodine they give aryloxymethyl aryloxyacetates (4) through the intermediacy of aryloxyacetyl hypoiodites and α-iodoanisoles.The former are unstable but have been trapped with pyridine to give N-iodopyridinium aryloxyacetates, whereas the latter are stable and react independently with compounds (3) to afford the acetates (4).The termolysis of (3) has been studied and, besides esters (4), aryl aryloxyacetates are also formed.The mechanism of the thermolysis is briefly discussed.