16492-74-3Relevant articles and documents
Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations
Dong, Xichang,Roeckl, Johannes L.,Waldvogel, Siegfried R.,Morandi, Bill
, (2021/02/12)
Vicinal dibromides and dichlorides are important commodity chemicals and indispensable synthetic intermediates in modern chemistry that are traditionally synthesized using hazardous elemental chlorine and bromine. Meanwhile, the environmental persistence of halogenated pollutants necessitates improved approaches to accelerate their remediation. Here, we introduce an electrochemically assisted shuttle (e-shuttle) paradigm for the facile and scalable interconversion of alkenes and vicinal dihalides, a class of reactions that can be used both to synthesize useful dihalogenated molecules from simple alkenes and to recycle waste material through retro-dihalogenation. The reaction is demonstrated using 1,2-dibromoethane, as well as 1,1,1,2-tetrachloroethane or 1,2-dichloroethane, to dibrominate or dichlorinate, respectively, a wide range of alkenes in a simple setup with inexpensive graphite electrodes. Conversely, the hexachlorinated persistent pollutant lindane could be fully dechlorinated to benzene in soil samples using simple alkene acceptors.
Vicinal dichlorination of olefins using NH4Cl and oxone
Swamy, Peraka,Reddy, Marri Mahender,Kumar, Macharla Arun,Naresh, Mameda,Narender, Nama
, p. 251 - 257 (2014/03/21)
A mild and efficient protocol for the preparation of 1,2-dichloroalkane derivatives from olefins using NH4Cl and Oxone at room temperature is described. A variety of terminal, internal, and cyclic alkenes reacted smoothly to give the corresponding dichlorinated products in good to excellent yields. Moreover, 1,2-disubstituted symmetrical and unsymmetrical olefins dichlorinated with moderate to excellent diastereoselectivity. This method precludes the use of acidic additives and transition metals in the synthesis of vicinal dichlorides.
Synthesis of chloroalkoxypyridinium salts by conjugate chlorination of unsaturated compounds in the presence of pyridine N-oxides
Britsun,Serguchev
, p. 789 - 793 (2007/10/03)
Conjugate chlorination of terminal alkenes in the presence of pyridine N-oxides yields mixtures of regioisomeric chloroalkoxypyridinium chlorides. The same reaction with internal arylalkenes is regioselective, but the resulting quaternary salt is a mixture of erythro and threo stereoisomers.
