Structures and thermal decomposition of some diphenyllead bispolyfluorobenzoates

P. G. Cookson, G. B. Deacon, P. W. Felder, G. J. Farquharson

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Abstract

The diphenyllead bispolyfluorobenzoates, Ph2Pb(O2CR)2 (R = C6F5, p-MeOC6F4 or p-EtOC6F4), obtained from diphenyllead diacetate and the appropriate polyfluorobenzoic acids, are considered to have associated structures with bridging bidentate carboxylate groups in the solid state and to be predominantly monomeric with chelating carboxylate groups at low concentrations in chloroform. Thermal decomposition of Ph2Pb(O2CC6F5)2 in boiling pyridine gave Ph2Pb(C6F5)2 and a low yield of Ph3PbC6F5, whereas Ph2Pb(O2C-p-MeOC6F4)2 and Ph2Pb(O2C-p-EtOC6F4)2 gave low yields of Ph3Pb-p-MeOC6F4 and Ph2Pb(p-EtOC6F4)2 respectively. From decomposition of Ph2Pb(O2CC6F5)2 under vacuum, Ph2Pb(C6F5)2, Ph3PbC6F5, Ph4Pb, PhC6F5, (C6F5)2CO and CO2 were obtained, whilst Ph4Pb, Ph2, PhR, RCO2Ph, R2CO and CO2 were detected from pyrolysis of Ph2Pb(O2CR)2 (R= p-MeOC6F4 or p-EtOC6F4). These compounds are formed by competing decarboxylation, rearrangement, and (under vacuum) homolysis reactions of the diorganolead dicarboxylates, and by further reactions of the rearrangement products.

Original languageEnglish
Pages (from-to)1895-1904
Number of pages10
JournalAustralian Journal of Chemistry
Volume27
Issue number9
DOIs
Publication statusPublished - 1 Jan 1974

Cite this

Cookson, P. G. ; Deacon, G. B. ; Felder, P. W. ; Farquharson, G. J. / Structures and thermal decomposition of some diphenyllead bispolyfluorobenzoates. In: Australian Journal of Chemistry. 1974 ; Vol. 27, No. 9. pp. 1895-1904.
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abstract = "The diphenyllead bispolyfluorobenzoates, Ph2Pb(O2CR)2 (R = C6F5, p-MeOC6F4 or p-EtOC6F4), obtained from diphenyllead diacetate and the appropriate polyfluorobenzoic acids, are considered to have associated structures with bridging bidentate carboxylate groups in the solid state and to be predominantly monomeric with chelating carboxylate groups at low concentrations in chloroform. Thermal decomposition of Ph2Pb(O2CC6F5)2 in boiling pyridine gave Ph2Pb(C6F5)2 and a low yield of Ph3PbC6F5, whereas Ph2Pb(O2C-p-MeOC6F4)2 and Ph2Pb(O2C-p-EtOC6F4)2 gave low yields of Ph3Pb-p-MeOC6F4 and Ph2Pb(p-EtOC6F4)2 respectively. From decomposition of Ph2Pb(O2CC6F5)2 under vacuum, Ph2Pb(C6F5)2, Ph3PbC6F5, Ph4Pb, PhC6F5, (C6F5)2CO and CO2 were obtained, whilst Ph4Pb, Ph2, PhR, RCO2Ph, R2CO and CO2 were detected from pyrolysis of Ph2Pb(O2CR)2 (R= p-MeOC6F4 or p-EtOC6F4). These compounds are formed by competing decarboxylation, rearrangement, and (under vacuum) homolysis reactions of the diorganolead dicarboxylates, and by further reactions of the rearrangement products.",
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Structures and thermal decomposition of some diphenyllead bispolyfluorobenzoates. / Cookson, P. G.; Deacon, G. B.; Felder, P. W.; Farquharson, G. J.

In: Australian Journal of Chemistry, Vol. 27, No. 9, 01.01.1974, p. 1895-1904.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Structures and thermal decomposition of some diphenyllead bispolyfluorobenzoates

AU - Cookson, P. G.

AU - Deacon, G. B.

AU - Felder, P. W.

AU - Farquharson, G. J.

PY - 1974/1/1

Y1 - 1974/1/1

N2 - The diphenyllead bispolyfluorobenzoates, Ph2Pb(O2CR)2 (R = C6F5, p-MeOC6F4 or p-EtOC6F4), obtained from diphenyllead diacetate and the appropriate polyfluorobenzoic acids, are considered to have associated structures with bridging bidentate carboxylate groups in the solid state and to be predominantly monomeric with chelating carboxylate groups at low concentrations in chloroform. Thermal decomposition of Ph2Pb(O2CC6F5)2 in boiling pyridine gave Ph2Pb(C6F5)2 and a low yield of Ph3PbC6F5, whereas Ph2Pb(O2C-p-MeOC6F4)2 and Ph2Pb(O2C-p-EtOC6F4)2 gave low yields of Ph3Pb-p-MeOC6F4 and Ph2Pb(p-EtOC6F4)2 respectively. From decomposition of Ph2Pb(O2CC6F5)2 under vacuum, Ph2Pb(C6F5)2, Ph3PbC6F5, Ph4Pb, PhC6F5, (C6F5)2CO and CO2 were obtained, whilst Ph4Pb, Ph2, PhR, RCO2Ph, R2CO and CO2 were detected from pyrolysis of Ph2Pb(O2CR)2 (R= p-MeOC6F4 or p-EtOC6F4). These compounds are formed by competing decarboxylation, rearrangement, and (under vacuum) homolysis reactions of the diorganolead dicarboxylates, and by further reactions of the rearrangement products.

AB - The diphenyllead bispolyfluorobenzoates, Ph2Pb(O2CR)2 (R = C6F5, p-MeOC6F4 or p-EtOC6F4), obtained from diphenyllead diacetate and the appropriate polyfluorobenzoic acids, are considered to have associated structures with bridging bidentate carboxylate groups in the solid state and to be predominantly monomeric with chelating carboxylate groups at low concentrations in chloroform. Thermal decomposition of Ph2Pb(O2CC6F5)2 in boiling pyridine gave Ph2Pb(C6F5)2 and a low yield of Ph3PbC6F5, whereas Ph2Pb(O2C-p-MeOC6F4)2 and Ph2Pb(O2C-p-EtOC6F4)2 gave low yields of Ph3Pb-p-MeOC6F4 and Ph2Pb(p-EtOC6F4)2 respectively. From decomposition of Ph2Pb(O2CC6F5)2 under vacuum, Ph2Pb(C6F5)2, Ph3PbC6F5, Ph4Pb, PhC6F5, (C6F5)2CO and CO2 were obtained, whilst Ph4Pb, Ph2, PhR, RCO2Ph, R2CO and CO2 were detected from pyrolysis of Ph2Pb(O2CR)2 (R= p-MeOC6F4 or p-EtOC6F4). These compounds are formed by competing decarboxylation, rearrangement, and (under vacuum) homolysis reactions of the diorganolead dicarboxylates, and by further reactions of the rearrangement products.

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U2 - 10.1071/CH9741895

DO - 10.1071/CH9741895

M3 - Article

VL - 27

SP - 1895

EP - 1904

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

SN - 0004-9425

IS - 9

ER -