7254-06-0Relevant articles and documents
Ring-closure reaction of 2-benzoylbenzenediazonium salts in 1-butyl-3- methylimidazolium ionic liquids
Okazaki, Takao,Yamamoto, Hiroyuki,Kitagawa, Toshikazu
, p. 50 - 59 (2018/02/07)
A ring-closure reaction by thermal dediazoniation of 2-substituted benzenediazonium tetrafluoroborates in imidazolium-based ionic liquids was investigated. Dediazoniation of 2-(4-R-benzoyl)benzenediazonium tetrafluoroborates (R = H, Me, OMe, Cl) in ionic liquid [BMIM][TfO] gave 3-R-9-fluorenones as ring-closure products and 2-(4-R-benzoyl)phenyl trifluoromethanesulfonates as substitution products. Dediazoniation in [BMIM][Tf2N] afforded 3-R-9-fluorenones and R-C6H4-CO-C6H4-OSO(CF3)(NSO2CF3). Yields of the ring-closure products were higher in [BMIM][Tf2N] than in [BMIM][TfO]. 2-Benzylbenzenediazonium and 2-phenoxybenzenediazonium tetrafluoroborates exclusively produced substitution products in both ionic liquids. DFT calculations suggest that electron transfer from the anion to render homolytic process should be induced more readily in [BMIM][Tf2N] than in [BMIM][TfO]. This ability may be responsible for the higher yields of the ring-closure products via homolytic pathway and the smaller yields of the substitution products via heterolytic pathway in [BMIM][Tf2N].