The reaction of 2-(chloromethyl)phenyl formamide, 2-(CH2Cl)C6H4NHCHO, with NaN3 in DMSO at room temperature affords 2-(azidomethyl)phenyl formamide, 2-(CH2N3)C6H4NHCHO (1), which is then dehydrated to 2-(azidomethyl)phenyl isocyanide, 2-(CH2N3)C6H4NC, (2) upon reaction with SOCl2 in DMF at low temperature. The coordination ability of the isocyanide 2 has been tested towards some Pt(II), Pd(II) and W(0) metal complexes to yield derivatives of the type [PtCl2(CNC6H4-2-CH2N3)2], [PdCl2(CNC6H4-2-CH2N3)(PPh3)] and [W(CO)5(CNC6H4-2-CH2N3)], respectively. (C) 2002 Elsevier Science B.V. All rights reserved.

Synthesis and transition metal coordination of 2-(azidomethyl)phenyl isocyanide

MICHELIN, RINO;MOZZON, MIRTO;SGARBOSSA, PAOLO;
2002

Abstract

The reaction of 2-(chloromethyl)phenyl formamide, 2-(CH2Cl)C6H4NHCHO, with NaN3 in DMSO at room temperature affords 2-(azidomethyl)phenyl formamide, 2-(CH2N3)C6H4NHCHO (1), which is then dehydrated to 2-(azidomethyl)phenyl isocyanide, 2-(CH2N3)C6H4NC, (2) upon reaction with SOCl2 in DMF at low temperature. The coordination ability of the isocyanide 2 has been tested towards some Pt(II), Pd(II) and W(0) metal complexes to yield derivatives of the type [PtCl2(CNC6H4-2-CH2N3)2], [PdCl2(CNC6H4-2-CH2N3)(PPh3)] and [W(CO)5(CNC6H4-2-CH2N3)], respectively. (C) 2002 Elsevier Science B.V. All rights reserved.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11577/2465310
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