56945-01-8Relevant articles and documents
Copper-catalyzed trifluoromethylation of internal olefinic C-H bonds: Efficient routes to trifluoromethylated tetrasubstituted olefins and N-heterocycles
Mao, Zhifeng,Huang, Fei,Yu, Haifeng,Chen, Jiping,Yu, Zhengkun,Xu, Zhaoqing
supporting information, p. 3439 - 3445 (2014/04/03)
The functionalization of internal olefins has been a challenging task in organic synthesis. Efficient CuII-catalyzed trifluoromethylation of internal olefins, that is, α-oxoketene dithioacetals, has been achieved by using Cu(OH)2 as a catalyst and TMSCF3 as a trifluoromethylating reagent. The push-pull effect from the polarized olefin substrates facilitates the internal olefinic C-H trifluoromethylation. Cyclic and acyclic dithioalkyl α-oxoketene acetals were used as the substrates and various substituents were tolerated. The internal olefinic C-H bond cleavage was not involved in the rate-determining step, and a mechanism that involves radicals is proposed based on a TEMPO-quenching experiment of the trifluoromethylation reaction. Further derivatization of the resultant CF 3 olefins led to multifunctionalized tetrasubstituted CF3 olefins and trifluoromethylated N-heterocycles.
The Synthesis of 4-Hydroxydithiocoumarins: A Case of Unusual Tautomer Stability
Anderson-McKay, Janet E.,Liepa, Andris J.
, p. 1179 - 1190 (2007/10/02)
2'-Chloroacetophenones react with carbon disulfide in the presence of sodium hydride to form 4-hydroxydithiocoumarin anions.Kinetic protonation provides the 4-hydroxydithiocoumarins which can be tautomerized to 2-mercapto-1-thiochromones by treatment with
