14121-36-9Relevant articles and documents
Polyhalogenoaromatic Compounds. Part 41. Photochemical Dehalogenation and Arylation Reactions of Polyhalogenoaromatic and Polyhalogenoheteroaromatic Compounds
Bratt, Jack,Iddon, Brian,Mack, Arthur G.,Suschitzky, Hans,Taylor, Jack A.,Wakefield, Basil J.
, p. 648 - 656 (2007/10/02)
Photolysis of pentachloro- and pentabromo-pyridine in diethyl ether or methanol leads to loss of β-halogen.A product (9) derived from attack on diethyl ether was also identified. 4-Bromotetrachloropyridine also undergoes loss of bromine and tetrachloro-4-iodopyridine loses iodine exclusively.Photodehalogenation of some perhalogenothiophens, tetrachloropyrimidine, and hexachlorobenzene is also described.Photolysis of pentachloroiodobenzene, tetrachloroiodopyridines, and trichloro-5-iodothiophen in benzene gives the corresponding polychloroaryl- or polychloroheteroaryl-benzenes.Photolysis of tetrachloro-4-(phenylthio)pyridine (3) gives 1,3,4-trichlorobenzothienopyridine (6), and the analogous perchloro(phenylthio)pyridine (37) gives the corresponding perchlorobenzothienopyridine (61).The scope of this type of photocyclisation has been explored; starting materials investigated include various arylthiopolyhalogenopyridines, some arylamino- and aryloxy-tetrachloropyridines, and 4-anilinotrichloropyrimidine.
Polyhalogenoaromatic Compounds. Part 43. Inter- and Intra-molecular Reactions of Polychloroaromatic Compounds with Copper
Mack, Arthur G.,Suschitzky, Hans,Wakefield, Basil J.
, p. 1682 - 1687 (2007/10/02)
The reaction of polychloroiodoarenes with copper in dimethylformamide gives good yields of the biaryls. 4-Bromotetrachloropyridine gives products of halogen exchange and reduction as well as coupling.Pentachloropyridine gave only tetrachloropyridines.Evidence against free radical or pyridyne intermediates is presented, and it is postulated that the reactions proceed via pyridylcopper compounds, although an electron transfer mechanism is not excluded.On reaction with copper, some 4-(o-halogenophenoxy)- and 4-(o-halogenothiophenoxy)-tetrahalogenopyridines give products of cyclisation, reduction, and halogen transfer.Copper reacts initially, at least in part, with the pyridyl group rather than with the o-halogenoaryl group.The results are again consistent with a reaction pathway involving a pyridylcopper intermediate.The products of nucleophilic substitution in pentahalogenopyridines by some phenols, thiophenols, and anilines are reported.
