TY - JOUR
T1 - Organomercury Compounds. XXIV Facile syntheses of polyfluoroarylmercurials by mercuration reactions
AU - Deacon, G. B.
AU - Tunaley, D.
PY - 1978/8/22
Y1 - 1978/8/22
N2 - The polyfluoroarylmercuric chlorides, RHgCl (R = C6F5, p-MeOC6F4, p-MeC6F4, m-HC6F4, o-HC6F4, p-HC6F4, m-O2NC6F4, o-O2NC6F4, p-BrC6F4, m-BrC6F4, o-BrC6F4, p-HOC6F4, p-H2NC6F4, m-HO2CC6F4, p-(p-HC6F4)C6F4, 3,5-H2C6F3, 3-bromo-2,4,6-trifluorophenyl or 3-bromo-2,5,6-trifluorophenyl), and the bis (polyfluorophenyl)mercurials, R2Hg (R = C6F5, p-MeOC6F4, p-MeC6F4, p-HC6F4, m-O2NC6F4,o-O2NC6F4, p-BrC6F4, m-BrC6F4, o-BrC6F4, p-HOC6F4, orp-H2NC6F4) have been prepared by mercuration of the appropriate polyfluoroarenes with mercuric trifluoroacetate and trifluoromethanesulphonic acid in trifluoroacetic acid, followed by treatment of the products with hydrochloric acid (RHgCl derivatives) or potassium bromide (R2Hg derivatives). For R = p-MeOC6F4, the actual mercuration product has been isolated and identified as 2,3,5,6-tetrafluoro-4-methoxyphenylmercuric trifluoromethane sulphonate. Interaction of mercuric trifluoroacetate with trifluoromethanesulphonic acid in trifluoroacetic acid yields mercuric trifluoromethanesulphonate, which is considered to be the mercurating agent, and which has been characterized as the complex, [Hg(bpy)3](O3SCF3)2·H20 (bpy = 2,2′-bipyridyl). The mercuration syntheses are very simple and convenient, and should become the preferred method for most polyfluoroarylmercurials.
AB - The polyfluoroarylmercuric chlorides, RHgCl (R = C6F5, p-MeOC6F4, p-MeC6F4, m-HC6F4, o-HC6F4, p-HC6F4, m-O2NC6F4, o-O2NC6F4, p-BrC6F4, m-BrC6F4, o-BrC6F4, p-HOC6F4, p-H2NC6F4, m-HO2CC6F4, p-(p-HC6F4)C6F4, 3,5-H2C6F3, 3-bromo-2,4,6-trifluorophenyl or 3-bromo-2,5,6-trifluorophenyl), and the bis (polyfluorophenyl)mercurials, R2Hg (R = C6F5, p-MeOC6F4, p-MeC6F4, p-HC6F4, m-O2NC6F4,o-O2NC6F4, p-BrC6F4, m-BrC6F4, o-BrC6F4, p-HOC6F4, orp-H2NC6F4) have been prepared by mercuration of the appropriate polyfluoroarenes with mercuric trifluoroacetate and trifluoromethanesulphonic acid in trifluoroacetic acid, followed by treatment of the products with hydrochloric acid (RHgCl derivatives) or potassium bromide (R2Hg derivatives). For R = p-MeOC6F4, the actual mercuration product has been isolated and identified as 2,3,5,6-tetrafluoro-4-methoxyphenylmercuric trifluoromethane sulphonate. Interaction of mercuric trifluoroacetate with trifluoromethanesulphonic acid in trifluoroacetic acid yields mercuric trifluoromethanesulphonate, which is considered to be the mercurating agent, and which has been characterized as the complex, [Hg(bpy)3](O3SCF3)2·H20 (bpy = 2,2′-bipyridyl). The mercuration syntheses are very simple and convenient, and should become the preferred method for most polyfluoroarylmercurials.
UR - http://www.scopus.com/inward/record.url?scp=0012480525&partnerID=8YFLogxK
U2 - 10.1016/S0022-328X(00)93546-0
DO - 10.1016/S0022-328X(00)93546-0
M3 - Article
AN - SCOPUS:0012480525
VL - 156
SP - 403
EP - 426
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
IS - 2
ER -