32616-83-4Relevant academic research and scientific papers
EPOXIDATION WITH THE H2O2/VILSMEIER REAGENT SYSTEM
Dulcere, Jean-Pierre,Rodriguez, Jean
, p. 1887 - 1888 (1982)
Alkenes 1 a-d interact at -80 deg C in 15 min. with the Vilsmeier reagent I (Me2N=CHCl)(+) PO2Cl2(-) in presence of 30percent H2O2 to yield the corresponding epoxides 3 a-d.The reaction could involve the formation of the highly reactive hydroperoxymethylenedimethylammonium salt (Me2N=CHOOH)(+) PO2Cl2(-) II.
The Electrochemical cis-Chlorination of Alkenes
Strehl, Julia,Fastie, Cornelius,Hilt, Gerhard
supporting information, p. 17341 - 17345 (2021/10/23)
The first example for the electrochemical cis-dichlorination of alkenes is presented. The reaction can be performed with little experimental effort by using phenylselenyl chloride as catalyst and tetrabutylammoniumchloride as supporting electrolyte, which also acts as nucleophilic reagent for the SN2-type replacement of selenium versus chloride. Cyclic voltammetric measurements and control experiments revealed a dual role of phenylselenyl chloride in the reaction. Based on these results a reaction mechanism was postulated, where the key step of the process is the activation of a phenylselenyl chloride-alkene adduct by electrochemically generated phenylselenyl trichloride. Like this, different aliphatic and aromatic cyclic and acyclic alkenes were converted to the dichlorinated products. Thereby, throughout high diastereoselectivities were achieved for the cis-chlorinated compounds of >95 : 5 or higher.
