Lithiation and dethiacarbonylation of a heterocyclic thioamide C 6H4O·C(=S)NH by reaction with solid Li2S in the presence of hexamethylphosphoramide: Synthesis and crystal structure of [c6H4O·C(=S)NLi·HMPA]2· C6H4(OH)NH2

David R. Armstrong; F. Adele Banbury; Matthew G. Davidson; Paul R. Raithby; Ronald Snaith; Dietmar Stalke

doi:10.1039/C39920001492

Lithiation and dethiacarbonylation of a heterocyclic thioamide C ₆H₄O·C(=S)NH by reaction with solid Li₂S in the presence of hexamethylphosphoramide: Synthesis and crystal structure of [c₆H₄O·C(=S)NLi·HMPA]₂· C₆H₄(OH)NH₂

David R. Armstrong
, F. Adele Banbury
, Matthew G. Davidson
, Paul R. Raithby
, Ronald Snaith
, Dietmar Stalke

University of Strathclyde
University of Cambridge
Institute for Inorganic Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Solid Li₂S reacts with a solution of C₆H ₄O·C(=S)NH and hexamethylphosphoramide (HMPA) in toluene to give [C₆H₄O·C(=S)NLi·μ₂-HMPA] ₂·C₆H₄(OH)NH₂, 1, in which two equivalents of the organic acid have been lithiated while a third equivalent has been stripped of its C=S group and di-protonated; structurally, complex 1, which can also be prepared directly by reacting BuⁿLi, C ₆H₄O·C(=S)NH, HMPA and NH₂C ₆H₄OH in 2:2:2:1 amounts, is unique in having a heterobifunctional ligand (NH₂C₆H₄OH) bridging two Li⁺ centres in the same molecule.

Original language	English
Pages (from-to)	1492-1494
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	20
DOIs	https://doi.org/10.1039/C39920001492
Publication status	Published - 1992

ASJC Scopus subject areas

Molecular Medicine

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Armstrong, D. R., Banbury, F. A., Davidson, M. G., Raithby, P. R., Snaith, R., & Stalke, D. (1992). Lithiation and dethiacarbonylation of a heterocyclic thioamide C ₆H₄O·C(=S)NH by reaction with solid Li₂S in the presence of hexamethylphosphoramide: Synthesis and crystal structure of [c₆H₄O·C(=S)NLi·HMPA]₂· C₆H₄(OH)NH₂. Journal of the Chemical Society, Chemical Communications, (20), 1492-1494. https://doi.org/10.1039/C39920001492

Lithiation and dethiacarbonylation of a heterocyclic thioamide C ₆H₄O·C(=S)NH by reaction with solid Li₂S in the presence of hexamethylphosphoramide: Synthesis and crystal structure of [c₆H₄O·C(=S)NLi·HMPA]₂· C₆H₄(OH)NH₂. / Armstrong, David R.; Banbury, F. Adele; Davidson, Matthew G. et al.
In: Journal of the Chemical Society, Chemical Communications, No. 20, 1992, p. 1492-1494.

Research output: Contribution to journal › Article › peer-review

Armstrong, DR, Banbury, FA, Davidson, MG , Raithby, PR, Snaith, R & Stalke, D 1992, 'Lithiation and dethiacarbonylation of a heterocyclic thioamide C ₆H₄O·C(=S)NH by reaction with solid Li₂S in the presence of hexamethylphosphoramide: Synthesis and crystal structure of [c₆H₄O·C(=S)NLi·HMPA]₂· C₆H₄(OH)NH₂', Journal of the Chemical Society, Chemical Communications, no. 20, pp. 1492-1494. https://doi.org/10.1039/C39920001492

Armstrong DR, Banbury FA, Davidson MG , Raithby PR, Snaith R, Stalke D. Lithiation and dethiacarbonylation of a heterocyclic thioamide C ₆H₄O·C(=S)NH by reaction with solid Li₂S in the presence of hexamethylphosphoramide: Synthesis and crystal structure of [c₆H₄O·C(=S)NLi·HMPA]₂· C₆H₄(OH)NH₂. Journal of the Chemical Society, Chemical Communications. 1992;(20):1492-1494. doi: 10.1039/C39920001492

Armstrong, David R. ; Banbury, F. Adele ; Davidson, Matthew G. et al. / Lithiation and dethiacarbonylation of a heterocyclic thioamide C ₆H₄O·C(=S)NH by reaction with solid Li₂S in the presence of hexamethylphosphoramide : Synthesis and crystal structure of [c₆H₄O·C(=S)NLi·HMPA]₂· C₆H₄(OH)NH₂. In: Journal of the Chemical Society, Chemical Communications. 1992 ; No. 20. pp. 1492-1494.

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title = "Lithiation and dethiacarbonylation of a heterocyclic thioamide C 6H4O·C(=S)NH by reaction with solid Li2S in the presence of hexamethylphosphoramide: Synthesis and crystal structure of [c6H4O·C(=S)NLi·HMPA]2· C6H4(OH)NH2",

abstract = "Solid Li2S reacts with a solution of C6H 4O·C(=S)NH and hexamethylphosphoramide (HMPA) in toluene to give [C6H4O·C(=S)NLi·μ2-HMPA] 2·C6H4(OH)NH2, 1, in which two equivalents of the organic acid have been lithiated while a third equivalent has been stripped of its C=S group and di-protonated; structurally, complex 1, which can also be prepared directly by reacting BunLi, C 6H4O·C(=S)NH, HMPA and NH2C 6H4OH in 2:2:2:1 amounts, is unique in having a heterobifunctional ligand (NH2C6H4OH) bridging two Li+ centres in the same molecule.",

author = "Armstrong, \{David R.\} and Banbury, \{F. Adele\} and Davidson, \{Matthew G.\} and Raithby, \{Paul R.\} and Ronald Snaith and Dietmar Stalke",

year = "1992",

doi = "10.1039/C39920001492",

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journal = "Journal of the Chemical Society, Chemical Communications",

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T1 - Lithiation and dethiacarbonylation of a heterocyclic thioamide C 6H4O·C(=S)NH by reaction with solid Li2S in the presence of hexamethylphosphoramide

T2 - Synthesis and crystal structure of [c6H4O·C(=S)NLi·HMPA]2· C6H4(OH)NH2

AU - Armstrong, David R.

AU - Banbury, F. Adele

AU - Davidson, Matthew G.

AU - Raithby, Paul R.

AU - Snaith, Ronald

AU - Stalke, Dietmar

PY - 1992

Y1 - 1992

N2 - Solid Li2S reacts with a solution of C6H 4O·C(=S)NH and hexamethylphosphoramide (HMPA) in toluene to give [C6H4O·C(=S)NLi·μ2-HMPA] 2·C6H4(OH)NH2, 1, in which two equivalents of the organic acid have been lithiated while a third equivalent has been stripped of its C=S group and di-protonated; structurally, complex 1, which can also be prepared directly by reacting BunLi, C 6H4O·C(=S)NH, HMPA and NH2C 6H4OH in 2:2:2:1 amounts, is unique in having a heterobifunctional ligand (NH2C6H4OH) bridging two Li+ centres in the same molecule.

AB - Solid Li2S reacts with a solution of C6H 4O·C(=S)NH and hexamethylphosphoramide (HMPA) in toluene to give [C6H4O·C(=S)NLi·μ2-HMPA] 2·C6H4(OH)NH2, 1, in which two equivalents of the organic acid have been lithiated while a third equivalent has been stripped of its C=S group and di-protonated; structurally, complex 1, which can also be prepared directly by reacting BunLi, C 6H4O·C(=S)NH, HMPA and NH2C 6H4OH in 2:2:2:1 amounts, is unique in having a heterobifunctional ligand (NH2C6H4OH) bridging two Li+ centres in the same molecule.

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