Unprecedented single-pot synthesis of nitrile-derived ketoimino platinum(II) complexes by ring opening of Δ4-1,2,4- oxadiazolines

M. Adília Januário Charmier; Matti Haukka; Armando J.L. Pombeiro

doi:10.1039/b406191h

Unprecedented single-pot synthesis of nitrile-derived ketoimino platinum(II) complexes by ring opening of Δ⁴-1,2,4- oxadiazolines

M. Adília Januário Charmier, Matti Haukka, Armando J.L. Pombeiro

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

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Abstract

[PtCl₂(RCN)₂] (1a R = CH₂CO₂Me, 1b R = CH₂Cl) prepared upon EtCN replacement at [PtCl ₂(EtCN)₂] by the appropriate organonitrile, react with a cyclic nitrone ^-O-⁺N=CHCH₂CH ₂C(Me)₂, under mild conditions, to give, in an unprecedented single-pot synthesis involving spontaneous N-O bond cleavage, the ketoimino complexes trans-[PtCl₂{RC(=O)N=CN-(H)C(Me) ₂-CH₂CH₂}₂] (2a, 2b) with two (pyrrolidin-2-ylidene)amino ligands. The analogous 2c (R = Et) and 2d (R = Ph) are formed by treatment with H₂, in the absence of any added catalyst, of the Δ⁴-1,2,4-oxadiazoline complexes trans-[PtCl₂-{N=C(R)ONC(Me)₂CH₂CH ₂CH}₂] (3a R = Et, 3b R = Ph) derived from the [2 + 3]-cycloaddition of the cyclic nitrone with the appropriate organonitrile complex of type 1. The compounds were characterized by elemental analyses, IR, ¹H, ¹³C and ¹⁹⁵Pt NMR spectroscopies, FAB mass spectrometry and X-ray structure analyses for 2a and 2d.

Original language	English
Pages (from-to)	2741-2745
Number of pages	5
Journal	Dalton Transactions
Issue number	17
DOIs	https://doi.org/10.1039/b406191h
Publication status	Published - 7 Sept 2004

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title = "Unprecedented single-pot synthesis of nitrile-derived ketoimino platinum(II) complexes by ring opening of Δ4-1,2,4- oxadiazolines",

abstract = "[PtCl2(RCN)2] (1a R = CH2CO2Me, 1b R = CH2Cl) prepared upon EtCN replacement at [PtCl 2(EtCN)2] by the appropriate organonitrile, react with a cyclic nitrone -O-+N=CHCH2CH 2C(Me)2, under mild conditions, to give, in an unprecedented single-pot synthesis involving spontaneous N-O bond cleavage, the ketoimino complexes trans-[PtCl2{RC(=O)N=CN-(H)C(Me) 2-CH2CH2}2] (2a, 2b) with two (pyrrolidin-2-ylidene)amino ligands. The analogous 2c (R = Et) and 2d (R = Ph) are formed by treatment with H2, in the absence of any added catalyst, of the Δ4-1,2,4-oxadiazoline complexes trans-[PtCl2-{N=C(R)ONC(Me)2CH2CH 2CH}2] (3a R = Et, 3b R = Ph) derived from the [2 + 3]-cycloaddition of the cyclic nitrone with the appropriate organonitrile complex of type 1. The compounds were characterized by elemental analyses, IR, 1H, 13C and 195Pt NMR spectroscopies, FAB mass spectrometry and X-ray structure analyses for 2a and 2d.",

author = "Charmier, {M. Ad{\'i}lia Janu{\'a}rio} and Matti Haukka and Pombeiro, {Armando J.L.}",

year = "2004",

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doi = "10.1039/b406191h",

language = "English",

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journal = "Dalton Transactions",

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T1 - Unprecedented single-pot synthesis of nitrile-derived ketoimino platinum(II) complexes by ring opening of Δ4-1,2,4- oxadiazolines

AU - Charmier, M. Adília Januário

AU - Haukka, Matti

AU - Pombeiro, Armando J.L.

PY - 2004/9/7

Y1 - 2004/9/7

N2 - [PtCl2(RCN)2] (1a R = CH2CO2Me, 1b R = CH2Cl) prepared upon EtCN replacement at [PtCl 2(EtCN)2] by the appropriate organonitrile, react with a cyclic nitrone -O-+N=CHCH2CH 2C(Me)2, under mild conditions, to give, in an unprecedented single-pot synthesis involving spontaneous N-O bond cleavage, the ketoimino complexes trans-[PtCl2{RC(=O)N=CN-(H)C(Me) 2-CH2CH2}2] (2a, 2b) with two (pyrrolidin-2-ylidene)amino ligands. The analogous 2c (R = Et) and 2d (R = Ph) are formed by treatment with H2, in the absence of any added catalyst, of the Δ4-1,2,4-oxadiazoline complexes trans-[PtCl2-{N=C(R)ONC(Me)2CH2CH 2CH}2] (3a R = Et, 3b R = Ph) derived from the [2 + 3]-cycloaddition of the cyclic nitrone with the appropriate organonitrile complex of type 1. The compounds were characterized by elemental analyses, IR, 1H, 13C and 195Pt NMR spectroscopies, FAB mass spectrometry and X-ray structure analyses for 2a and 2d.

AB - [PtCl2(RCN)2] (1a R = CH2CO2Me, 1b R = CH2Cl) prepared upon EtCN replacement at [PtCl 2(EtCN)2] by the appropriate organonitrile, react with a cyclic nitrone -O-+N=CHCH2CH 2C(Me)2, under mild conditions, to give, in an unprecedented single-pot synthesis involving spontaneous N-O bond cleavage, the ketoimino complexes trans-[PtCl2{RC(=O)N=CN-(H)C(Me) 2-CH2CH2}2] (2a, 2b) with two (pyrrolidin-2-ylidene)amino ligands. The analogous 2c (R = Et) and 2d (R = Ph) are formed by treatment with H2, in the absence of any added catalyst, of the Δ4-1,2,4-oxadiazoline complexes trans-[PtCl2-{N=C(R)ONC(Me)2CH2CH 2CH}2] (3a R = Et, 3b R = Ph) derived from the [2 + 3]-cycloaddition of the cyclic nitrone with the appropriate organonitrile complex of type 1. The compounds were characterized by elemental analyses, IR, 1H, 13C and 195Pt NMR spectroscopies, FAB mass spectrometry and X-ray structure analyses for 2a and 2d.

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DO - 10.1039/b406191h

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Unprecedented single-pot synthesis of nitrile-derived ketoimino platinum(II) complexes by ring opening of Δ⁴-1,2,4- oxadiazolines

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