Welcome to LookChem.com Sign In|Join Free

Article Doi

Studies on Organic Fluorine Compounds. Part 27. Abnormal Reactions in the Trifluoromethylation of Aromatic Compounds with Trifluoromethyl Iodide and Copper Powder

DOI: 10.1039/P19800000661

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 661 - 664 (1980)

Update date:2022-08-04

Topics:

Authors:

Kobayashi, YoshiroKobayashi, Yoshiro

Kumadaki, ItsumaroKumadaki, Itsumaro

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19800000661

Reaction of 3-bromobenzofuran with trifluoromethyl iodide and copper powder in pyridine gave 2-(trifluoromethyl)-, 2- and 3-(pentafluoroethyl)-, and 2,3-bis(trifluoromethyl)-benzofuran, as well as the expected product, 3-(trifluoromethyl)benzofuran.Bromoanisole also gave (trifluoromethyl)anisole and (pentafluoroethyl)anisole, but introduction of the perfluoroalkyl group occurred at the position originally occupied by the bromine.Formation of pentafluoroethyl compounds is explained by decomposition of trifluoromethylcopper to cuprous fluoride and difluorocarbene, which can then react with a further molecule of trifluoromethylcopper to form pentafluoroethylcopper.This then reacts with aryl halide to give pentafluoroethyl compounds.Perfluoroalkylcopper is thermally cleaved to perfluoroalkyl radical, which then reacts with pyridine to give perfluoroalkylpyridines.This mechanism must be involved in the formation of 2,3-bis(trifluoromethyl)benzofuran.Introduction of a perfluoroalkyl group to the position originally unoccupied with halogen might be due to the rather localized double bond in benzofuran.

View More

Products guided by the article

Product name:Benzofuran, 2,3-bis(trifluoromethyl)-

Cas No:74881-64-4

74881-64-4

R&D Labs maybe for 74881-64-4

Relevant to this article

Hot Product