Organolanthanoids. IV some reactions of bis(polyfluorophenyl)ytterbium compounds

Glen B. Deacon; Peter I. Mackinnon; Tran D. Tuong

doi:10.1071/CH9830043

Organolanthanoids. IV some reactions of bis(polyfluorophenyl)ytterbium compounds

Glen B. Deacon, Peter I. Mackinnon, Tran D. Tuong

School of Chemistry

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Abstract

From reactions of bis(polyfluorophenyl)ytterbium compounds R₂Yb (R = C₆F₅or p-HC₆F₄) with trans-Rh(CO)Cl(PPh₃)₂, NiCl₂(bpy) (bpy = 2,2’-bipyridyl), NiCl₂(PPh₃)₂, PtCl₂(bpy), triphenyltin chloride, iodine and mercuric chloride, the polyfluorophenyl derivatives trans-RRh(CO)(PPh₃)₂, R₂Ni(bpy), trans-(C₆F₅)₂Ni(PPh₃)₂, (C₆F₅)₂Pt(bpy), Ph₃SnC₆F₅, C₆F₅I and (C₆F₅)₂Hg have been obtained. Reduction to mercury metal accompanied formation of the last compound. Carbonation of (C₆F₅)₂Yb in tetrahydrofuran followed by acidification yields pentafluorobenzoic acid and, surprisingly, a significant amount of 2,3,4,5-tetrafluorobenzoic acid, in which the aromatic hydrogen is substantially derived from tetrahydrofuran. Reaction of (C₆F₅)₂Yb with pentafluorobenzoic acid followed by acidification also gives 2,3,4,5-tetrafluorobenzoic acid. Fluoride elimination is less extensive and less specific in a similar reaction of YbI₂.

Original language	English
Pages (from-to)	43-53
Number of pages	11
Journal	Australian Journal of Chemistry
Volume	36
Issue number	1
DOIs	https://doi.org/10.1071/CH9830043
Publication status	Published - 1983

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10.1071/CH9830043

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@article{d16e55a67b3d41c3a42e08c9fec6771b,

title = "Organolanthanoids. IV some reactions of bis(polyfluorophenyl)ytterbium compounds",

abstract = "From reactions of bis(polyfluorophenyl)ytterbium compounds R2Yb (R = C6F5or p-HC6F4) with trans-Rh(CO)Cl(PPh3)2, NiCl2(bpy) (bpy = 2,2{\textquoteright}-bipyridyl), NiCl2(PPh3)2, PtCl2(bpy), triphenyltin chloride, iodine and mercuric chloride, the polyfluorophenyl derivatives trans-RRh(CO)(PPh3)2, R2Ni(bpy), trans-(C6F5)2Ni(PPh3)2, (C6F5)2Pt(bpy), Ph3SnC6F5, C6F5I and (C6F5)2Hg have been obtained. Reduction to mercury metal accompanied formation of the last compound. Carbonation of (C6F5)2Yb in tetrahydrofuran followed by acidification yields pentafluorobenzoic acid and, surprisingly, a significant amount of 2,3,4,5-tetrafluorobenzoic acid, in which the aromatic hydrogen is substantially derived from tetrahydrofuran. Reaction of (C6F5)2Yb with pentafluorobenzoic acid followed by acidification also gives 2,3,4,5-tetrafluorobenzoic acid. Fluoride elimination is less extensive and less specific in a similar reaction of YbI2. ",

author = "Deacon, {Glen B.} and Mackinnon, {Peter I.} and Tuong, {Tran D.}",

year = "1983",

doi = "10.1071/CH9830043",

language = "English",

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pages = "43--53",

journal = "Australian Journal of Chemistry",

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T1 - Organolanthanoids. IV some reactions of bis(polyfluorophenyl)ytterbium compounds

AU - Deacon, Glen B.

AU - Mackinnon, Peter I.

AU - Tuong, Tran D.

PY - 1983

Y1 - 1983

N2 - From reactions of bis(polyfluorophenyl)ytterbium compounds R2Yb (R = C6F5or p-HC6F4) with trans-Rh(CO)Cl(PPh3)2, NiCl2(bpy) (bpy = 2,2’-bipyridyl), NiCl2(PPh3)2, PtCl2(bpy), triphenyltin chloride, iodine and mercuric chloride, the polyfluorophenyl derivatives trans-RRh(CO)(PPh3)2, R2Ni(bpy), trans-(C6F5)2Ni(PPh3)2, (C6F5)2Pt(bpy), Ph3SnC6F5, C6F5I and (C6F5)2Hg have been obtained. Reduction to mercury metal accompanied formation of the last compound. Carbonation of (C6F5)2Yb in tetrahydrofuran followed by acidification yields pentafluorobenzoic acid and, surprisingly, a significant amount of 2,3,4,5-tetrafluorobenzoic acid, in which the aromatic hydrogen is substantially derived from tetrahydrofuran. Reaction of (C6F5)2Yb with pentafluorobenzoic acid followed by acidification also gives 2,3,4,5-tetrafluorobenzoic acid. Fluoride elimination is less extensive and less specific in a similar reaction of YbI2.

AB - From reactions of bis(polyfluorophenyl)ytterbium compounds R2Yb (R = C6F5or p-HC6F4) with trans-Rh(CO)Cl(PPh3)2, NiCl2(bpy) (bpy = 2,2’-bipyridyl), NiCl2(PPh3)2, PtCl2(bpy), triphenyltin chloride, iodine and mercuric chloride, the polyfluorophenyl derivatives trans-RRh(CO)(PPh3)2, R2Ni(bpy), trans-(C6F5)2Ni(PPh3)2, (C6F5)2Pt(bpy), Ph3SnC6F5, C6F5I and (C6F5)2Hg have been obtained. Reduction to mercury metal accompanied formation of the last compound. Carbonation of (C6F5)2Yb in tetrahydrofuran followed by acidification yields pentafluorobenzoic acid and, surprisingly, a significant amount of 2,3,4,5-tetrafluorobenzoic acid, in which the aromatic hydrogen is substantially derived from tetrahydrofuran. Reaction of (C6F5)2Yb with pentafluorobenzoic acid followed by acidification also gives 2,3,4,5-tetrafluorobenzoic acid. Fluoride elimination is less extensive and less specific in a similar reaction of YbI2.

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