Organomercury compounds. XVII. The mercuration of 1,2,3,4-tetrafluorobenzene, 1,2,3,5-tetrafluorobenzene, 2,3,5,6-tetrafluoroanisole, and 2,3,4,5-tetrafluoronitrobenzene

H. B. Albrecht, G. B. Deacon

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Abstract

The tetrafluorophenylmercuric trifluoroacetates, RHgO2CCF3 (R = o-HC6F4, m-HC6F4, p-MeOC6F4, or o-O2NC6F4), and the dimercurated tetrafluorobenzenes o-(CF3CO2Hg)2C6F4 and m-(CF3CO2Hg)2C6F4 have been prepared by mercuration of the appropriate tetrafluorobenzenes with mercuric trifluoroacetate. Reaction of 1,2,3,4-tetrafluorobenzene with mercuric acetate did not give pure monomercurated or dimercurated products, but o-HC6F4HgO2CCH3 and o-(CH3CO2Hg)2C6F4 were obtained analytically pure by treatment of the appropriate trifluoroacetates with acetic acid. The diarylmercurials R2Hg (R = o-HC6F4, m-HC6F4, p-MeOC6F4, or o-O2NC6F4) were prepared by symmetrization of the tetrafluorophenylmercuric trifluoroacetates with iodide or bromide ions in methanol or aqueous methanol. A good yield of (p-MeOC6F4)2Hg, and low yields of crude (m-HC6F4)2Hg and (o-O2NC6F4)2Hg were obtained by mercuration of the corresponding tetrafluorobenzenes under basic conditions, but (o-HC6F4)2Hg could not be obtained by this method. The halogeno derivatives RHgX (R = o-HC6F4 or m-HC6F4), o-(XHg)2C6F4, and m-(XHg)2C6F4 (X = Cl or Br) have been synthesized from the appropriate trifluoroacetates and hydrogen halides and/or by redistribution reactions of suitable mercurials and mercuric halides.

Original languageEnglish
Pages (from-to)77-86
Number of pages10
JournalJournal of Organometallic Chemistry
Volume57
Issue number1
DOIs
Publication statusPublished - 16 Aug 1973

Cite this

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title = "Organomercury compounds. XVII. The mercuration of 1,2,3,4-tetrafluorobenzene, 1,2,3,5-tetrafluorobenzene, 2,3,5,6-tetrafluoroanisole, and 2,3,4,5-tetrafluoronitrobenzene",
abstract = "The tetrafluorophenylmercuric trifluoroacetates, RHgO2CCF3 (R = o-HC6F4, m-HC6F4, p-MeOC6F4, or o-O2NC6F4), and the dimercurated tetrafluorobenzenes o-(CF3CO2Hg)2C6F4 and m-(CF3CO2Hg)2C6F4 have been prepared by mercuration of the appropriate tetrafluorobenzenes with mercuric trifluoroacetate. Reaction of 1,2,3,4-tetrafluorobenzene with mercuric acetate did not give pure monomercurated or dimercurated products, but o-HC6F4HgO2CCH3 and o-(CH3CO2Hg)2C6F4 were obtained analytically pure by treatment of the appropriate trifluoroacetates with acetic acid. The diarylmercurials R2Hg (R = o-HC6F4, m-HC6F4, p-MeOC6F4, or o-O2NC6F4) were prepared by symmetrization of the tetrafluorophenylmercuric trifluoroacetates with iodide or bromide ions in methanol or aqueous methanol. A good yield of (p-MeOC6F4)2Hg, and low yields of crude (m-HC6F4)2Hg and (o-O2NC6F4)2Hg were obtained by mercuration of the corresponding tetrafluorobenzenes under basic conditions, but (o-HC6F4)2Hg could not be obtained by this method. The halogeno derivatives RHgX (R = o-HC6F4 or m-HC6F4), o-(XHg)2C6F4, and m-(XHg)2C6F4 (X = Cl or Br) have been synthesized from the appropriate trifluoroacetates and hydrogen halides and/or by redistribution reactions of suitable mercurials and mercuric halides.",
author = "Albrecht, {H. B.} and Deacon, {G. B.}",
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T1 - Organomercury compounds. XVII. The mercuration of 1,2,3,4-tetrafluorobenzene, 1,2,3,5-tetrafluorobenzene, 2,3,5,6-tetrafluoroanisole, and 2,3,4,5-tetrafluoronitrobenzene

AU - Albrecht, H. B.

AU - Deacon, G. B.

PY - 1973/8/16

Y1 - 1973/8/16

N2 - The tetrafluorophenylmercuric trifluoroacetates, RHgO2CCF3 (R = o-HC6F4, m-HC6F4, p-MeOC6F4, or o-O2NC6F4), and the dimercurated tetrafluorobenzenes o-(CF3CO2Hg)2C6F4 and m-(CF3CO2Hg)2C6F4 have been prepared by mercuration of the appropriate tetrafluorobenzenes with mercuric trifluoroacetate. Reaction of 1,2,3,4-tetrafluorobenzene with mercuric acetate did not give pure monomercurated or dimercurated products, but o-HC6F4HgO2CCH3 and o-(CH3CO2Hg)2C6F4 were obtained analytically pure by treatment of the appropriate trifluoroacetates with acetic acid. The diarylmercurials R2Hg (R = o-HC6F4, m-HC6F4, p-MeOC6F4, or o-O2NC6F4) were prepared by symmetrization of the tetrafluorophenylmercuric trifluoroacetates with iodide or bromide ions in methanol or aqueous methanol. A good yield of (p-MeOC6F4)2Hg, and low yields of crude (m-HC6F4)2Hg and (o-O2NC6F4)2Hg were obtained by mercuration of the corresponding tetrafluorobenzenes under basic conditions, but (o-HC6F4)2Hg could not be obtained by this method. The halogeno derivatives RHgX (R = o-HC6F4 or m-HC6F4), o-(XHg)2C6F4, and m-(XHg)2C6F4 (X = Cl or Br) have been synthesized from the appropriate trifluoroacetates and hydrogen halides and/or by redistribution reactions of suitable mercurials and mercuric halides.

AB - The tetrafluorophenylmercuric trifluoroacetates, RHgO2CCF3 (R = o-HC6F4, m-HC6F4, p-MeOC6F4, or o-O2NC6F4), and the dimercurated tetrafluorobenzenes o-(CF3CO2Hg)2C6F4 and m-(CF3CO2Hg)2C6F4 have been prepared by mercuration of the appropriate tetrafluorobenzenes with mercuric trifluoroacetate. Reaction of 1,2,3,4-tetrafluorobenzene with mercuric acetate did not give pure monomercurated or dimercurated products, but o-HC6F4HgO2CCH3 and o-(CH3CO2Hg)2C6F4 were obtained analytically pure by treatment of the appropriate trifluoroacetates with acetic acid. The diarylmercurials R2Hg (R = o-HC6F4, m-HC6F4, p-MeOC6F4, or o-O2NC6F4) were prepared by symmetrization of the tetrafluorophenylmercuric trifluoroacetates with iodide or bromide ions in methanol or aqueous methanol. A good yield of (p-MeOC6F4)2Hg, and low yields of crude (m-HC6F4)2Hg and (o-O2NC6F4)2Hg were obtained by mercuration of the corresponding tetrafluorobenzenes under basic conditions, but (o-HC6F4)2Hg could not be obtained by this method. The halogeno derivatives RHgX (R = o-HC6F4 or m-HC6F4), o-(XHg)2C6F4, and m-(XHg)2C6F4 (X = Cl or Br) have been synthesized from the appropriate trifluoroacetates and hydrogen halides and/or by redistribution reactions of suitable mercurials and mercuric halides.

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U2 - 10.1016/S0022-328X(00)89656-4

DO - 10.1016/S0022-328X(00)89656-4

M3 - Article

VL - 57

SP - 77

EP - 86

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 1

ER -