Dichlorination of olefins with trichloroisocyanuric acid (TCCA) and tetrabutylammonium chloride (TBACl)


Koçak R.

Organic and Biomolecular Chemistry, cilt.23, sa.8, ss.1894-1900, 2025 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 23 Sayı: 8
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1039/d4ob01962h
  • Dergi Adı: Organic and Biomolecular Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, Compendex, MEDLINE, Veterinary Science Database
  • Sayfa Sayıları: ss.1894-1900
  • Atatürk Üniversitesi Adresli: Hayır

Özet

Herein, a new metal-free, molecular chlorine-free, environmentally friendly, atom-economical, short time, inexpensive and simple operation method with mild reaction conditions for chlorination of alkenes, cyclic alkenes, α,β-unsaturated carbonyl compounds, heteroaromatics, and natural products was reported with up to 96% yields using trichloroisocyanuric acid (TCCA) as the electrophilic chlorine source and TBACl as the nucleophilic chlorine source. It was demonstrated with bicyclic alkene benzonorbornadiene that regioselective chlorobromination and dibromination reactions can be carried out through TCCA/TBABr redox reactions, where TCCA acts as an oxidant in the presence of TBABr. The structures of the redox products were confirmed as a result of control experiments conducted with the newly presented DBI/TBACl and DBI/TBABr halogenation pairs.