Synthesis, Crystal Structures, and Reactions of 2-Oxomalonylbis(arylimidoyl) Chlorides and Hydroxymethane Tris(arylimidoyl) Chlorides

Richard J. Bowen; Judy Caddy; Mabel E. Coyanis; Manuel A. Fernandes; Marcus Layh; Linda Z. Linganiso; Winny K. Maboya; Bernard Omondi

doi:10.1071/CH04263

RESEARCH ARTICLE

Synthesis, Crystal Structures, and Reactions of 2-Oxomalonylbis(arylimidoyl) Chlorides and Hydroxymethane Tris(arylimidoyl) Chlorides

Richard J. Bowen ^A ^B , Judy Caddy ^A ^B , Mabel E. Coyanis ^A , Manuel A. Fernandes ^A , Marcus Layh ^A ^C , Linda Z. Linganiso ^A , Winny K. Maboya ^A and Bernard Omondi ^A

+ Author Affiliations

- Author Affiliations

^A Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, Wits Johannesburg 2050, South Africa.

^B Project AuTEK, Mintek, Private Bag X 3015, Randburg 2125, South Africa.

^C Corresponding author. Email: marcus@aurum.wits.ac.za

Australian Journal of Chemistry 58(7) 522-530 https://doi.org/10.1071/CH04263
Submitted: 6 November 2004 Accepted: 25 March 2005 Published: 21 July 2005

Abstract

The 2-oxomalonylbis(arylimidoyl) chlorides [C₆H₃(R₂-2,6)N=CCl]₂CO (R = Me, 3a; Prⁱ, 3b; H, 3c) were synthesized from C₆H₃(R₂-2,6)NHCHO and an excess of (COCl₂)₃ and their reaction with various nucleophiles was studied. Successive hydrolysis of 3a led to the formation of [C₆H₃(Me₂-2,6)N=CCl]₃COH 4a and [C₆H₃(Me₂-2,6)NHCO]₃COH 5a, while treatment of 3a with HAuCl₄(H₂O)_x gave {[C₆H₃(Me₂-2,6)N(H)=CCl][C₆H₃(Me₂-2,6)NHCO]₂COH}AuCl₄ 6a. All compounds were fully characterized by microanalysis, NMR spectroscopy, mass spectrometry, and, in the case of 3a, 4a, 5a, and 6a, by X-ray crystallography.

Acknowledgments

The authors thank Mintek (project AuTEK), the Claude Harris Leon foundation (postdoctoral research fellowship for R.J.B.), and the University of the Witwatersrand for financial support, Mr Ian Vorster (Rand Afrikaans University) for carrying out the mass spectrometry analyses, and Professor D. Reid for helpful discussions.

References

Synthesis, Crystal Structures, and Reactions of 2-Oxomalonylbis(arylimidoyl) Chlorides and Hydroxymethane Tris(arylimidoyl) Chlorides

Abstract

Acknowledgments

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