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Synthesis of azetidinylidene complexes from [(CO)5M(CH2Cl2)], phenylacetylene and imines and oxidative decomplexation to give β-lactams

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1999

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Abd-Elzaher, Mokhles M.

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Journal of Organometallic Chemistry. 1999, 588(2), pp. 235-241. ISSN 0022-328X. eISSN 1872-8561. Available under: doi: 10.1016/S0022-328X(99)00381-2

Zusammenfassung

Photolysis of [M(CO)6] in CH2Cl2 gives [(CO)5M(CH2Cl2)]. Substitution of phenylacetylene for CH2Cl2 produces the thermolabile phenylacetylene complexes [(CO)5M(HCCPh)] [M=Cr (1), Mo (2), W (3)]. Addition of N-alkyl benzylideneimines, RNC(Ph)H, to solutions of 1–3 affords the 2-azetidin-1-ylidene complexes [(CO)5MView the MathML source(Ph)H] [M=Cr, Mo, W; R=Et, i-Pr]. The reaction presumably proceeds by cycloaddition of the imines to the CC bond of vinylidene complexes resulting from tautomerization of the alkyne complexes. The cycloaddition is highly stereoselective. Predominantly, the syn isomer is obtained (syn/anti≥9). The reaction of 3 with dialkylcarbodimides, RNCNR (R=c-Hex, i-Pr), yields 3-imino-2-azetidin-1-ylidene complexes, [(CO)5WView the MathML source(Ph)H]. By oxidative cleavage of the CrC bond in [(CO)5CrView the MathML source(Ph)H] the corresponding β-lactams are obtained in high yields.

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540 Chemie

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Azetidinylidene complexes, Oxidative decomplexation, β-lactams

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ISO 690ABD-ELZAHER, Mokhles M., Helmut FISCHER, 1999. Synthesis of azetidinylidene complexes from [(CO)5M(CH2Cl2)], phenylacetylene and imines and oxidative decomplexation to give β-lactams. In: Journal of Organometallic Chemistry. 1999, 588(2), pp. 235-241. ISSN 0022-328X. eISSN 1872-8561. Available under: doi: 10.1016/S0022-328X(99)00381-2
BibTex
@article{AbdElzaher1999Synth-23036,
  year={1999},
  doi={10.1016/S0022-328X(99)00381-2},
  title={Synthesis of azetidinylidene complexes from [(CO)5M(CH2Cl2)], phenylacetylene and imines and oxidative decomplexation to give β-lactams},
  number={2},
  volume={588},
  issn={0022-328X},
  journal={Journal of Organometallic Chemistry},
  pages={235--241},
  author={Abd-Elzaher, Mokhles M. and Fischer, Helmut}
}
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    <dcterms:abstract xml:lang="eng">Photolysis of [M(CO)6] in CH2Cl2 gives [(CO)5M(CH2Cl2)]. Substitution of phenylacetylene for CH2Cl2 produces the thermolabile phenylacetylene complexes [(CO)5M(HCCPh)] [M=Cr (1), Mo (2), W (3)]. Addition of N-alkyl benzylideneimines, RNC(Ph)H, to solutions of 1–3 affords the 2-azetidin-1-ylidene complexes [(CO)5MView the MathML source(Ph)H] [M=Cr, Mo, W; R=Et, i-Pr]. The reaction presumably proceeds by cycloaddition of the imines to the CC bond of vinylidene complexes resulting from tautomerization of the alkyne complexes. The cycloaddition is highly stereoselective. Predominantly, the syn isomer is obtained (syn/anti≥9). The reaction of 3 with dialkylcarbodimides, RNCNR (R=c-Hex, i-Pr), yields 3-imino-2-azetidin-1-ylidene complexes, [(CO)5WView the MathML source(Ph)H]. By oxidative cleavage of the CrC bond in [(CO)5CrView the MathML source(Ph)H] the corresponding β-lactams are obtained in high yields.</dcterms:abstract>
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