103224-67-5Relevant academic research and scientific papers
Synthesis of Diverse Aromatic Ketones through C?F Cleavage of Trifluoromethyl Group
Ikeda, Mai,Matsuzawa, Tsubasa,Morita, Takamoto,Hosoya, Takamitsu,Yoshida, Suguru
supporting information, p. 12333 - 12337 (2020/09/09)
An efficient synthetic method of aromatic ketones through C?F cleavage of trifluoromethyl group is disclosed. The high functional group tolerance of the transformation and the remarkable stability of trifluoromethyl group in various reactions enabled mult
Isolation, X-ray structures, and electronic spectra of reactive intermediates in Friedel-Crafts acylations
Davlieva,Lindeman,Neretin,Kochi
, p. 4013 - 4021 (2007/10/03)
Reactive intermediates in the Friedel-Crafts acylation of aromatic donors are scrutinized upon their successful isolation and X-ray crystallography at very low temperatures. Detailed analyses of the X-ray parameters for the [1:1] complexes of different al
Positional Reactivity of Acylpolymethylbenzenes in Electrophilic Substitution
Matsuura, Kazunori,Kimura, Yasuo,Takahashi, Hisakazu,Morita, Toshio,Takahashi, Ichiro,et al.
, p. 757 - 765 (2007/10/02)
Friedel-Crafts acylation, bromination, deuteration, and nitration of acetylpentamethylbenzene (APMB), 1-acetyl-2,3,4,6-tetramethylbenzene (ATMB), and 1-benzoyl-2,3,4,6-tetramethylbenzene (BTMB) and the resulting product distribution were investigated.Friedel-Crafts acylation, bromination, and deuteration of APMB and Friedel-Crafts acylation of ATMB gave deacetylation-substitution products.On the other hand, bromination and deuteration of ATMB (or BTMB) and Friedel-Crafts acylation of BTMB gave 5-substituted products.In both cases, the positional reactivities were in accordance with the relative ?-complex stability.Conversely, except for Friedel-Crafts-type nitration, the positional reactivities in the nitration of these substrates were strikingly different from those of the above three reactions.Thus, side-chain functionalization at the 6-methyl group occurred in nitration with fuming nitric acid, depending on the solvents in use.The NMDO calculations and the reaction of APMB with single-electron transfer reagents such as tetranitromethane-hν or cerium(IV) ammonium nitrate suggest that the product distribution in nitration can be explained in terms of a single-electron transfer mechanism.
