Ethynylthioamide Complexes : Synthesis, Reactivity and an Unusual Coupling Reaction with Diethylaminopropyne

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2007
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Szesni, Normen
Drexler, Matthias
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Zeitschrift für Naturforschung B. 2007, 62(3), pp. 346-356. ISSN 0932-0776. eISSN 1865-7117. Available under: doi: 10.1515/znb-2007-0307
Zusammenfassung

The reaction of [(CO)5Cr(THF)] with propynethioic acid amides, R–C≡C–C(=S)NMe2 (R = H, SiMe3), yields the thioamide complexes [(CO)5Cr–S=C(NMe2)C≡C–H] (1a) and [(CO)5Cr–S=C(NMe2)C≡C–SiMe3] (1b). Treatment of solutions of 1a or 1b with methyllithium generates, via deprotonation or desilylation, the lithium salt Li[(CO)5Cr–S=C(NMe2)C≡C] (2). On filtration over silica, 2 is readily reprotonated. Complex 1a is inert towards methanol, however, adds diethylamine across the C≡C bond to give the thioacrylamide complex [(CO)5Cr–=C(NMe2)C(H)=C(H)NMe2] (3). Thiourea displaces the thioamide ligand to give [(CO)5Cr–S=C(NH2)2] (4). Complex 1a reacts with half an equivalent of diethylaminopropyne in a three-component coupling to form the homobinuclear complex [(CO)5Cr–=C(NEt2)–C(CH3)=C(H)–C(H)=C(NMe2)–C≡C–C(NMe2)=S–Cr(CO)5] (5) in high yield. The solid state structures of complexes 1a and 5 were established by X-ray structural analyses.

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ISO 690SZESNI, Normen, Matthias DREXLER, Bernhard WEIBERT, Helmut FISCHER, 2007. Ethynylthioamide Complexes : Synthesis, Reactivity and an Unusual Coupling Reaction with Diethylaminopropyne. In: Zeitschrift für Naturforschung B. 2007, 62(3), pp. 346-356. ISSN 0932-0776. eISSN 1865-7117. Available under: doi: 10.1515/znb-2007-0307
BibTex
@article{Szesni2007Ethyn-22895,
  year={2007},
  doi={10.1515/znb-2007-0307},
  title={Ethynylthioamide Complexes : Synthesis, Reactivity and an Unusual Coupling Reaction with Diethylaminopropyne},
  number={3},
  volume={62},
  issn={0932-0776},
  journal={Zeitschrift für Naturforschung B},
  pages={346--356},
  author={Szesni, Normen and Drexler, Matthias and Weibert, Bernhard and Fischer, Helmut}
}
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    <dcterms:abstract xml:lang="eng">The reaction of [(CO)&lt;sub&gt;5&lt;/sub&gt;Cr(THF)] with propynethioic acid amides, R–C≡C–C(=S)NMe&lt;sub&gt;2&lt;/sub&gt; (R = H, SiMe&lt;sub&gt;3&lt;/sub&gt;), yields the thioamide complexes [(CO)&lt;sub&gt;5&lt;/sub&gt;Cr–S=C(NMe&lt;sub&gt;2&lt;/sub&gt;)C≡C–H] (1a) and [(CO)&lt;sub&gt;5&lt;/sub&gt;Cr–S=C(NMe&lt;sub&gt;2&lt;/sub&gt;)C≡C–SiMe&lt;sub&gt;3&lt;/sub&gt;] (1b). Treatment of solutions of 1a or 1b with methyllithium generates, via deprotonation or desilylation, the lithium salt Li[(CO)&lt;sub&gt;5&lt;/sub&gt;Cr–S=C(NMe&lt;sub&gt;2&lt;/sub&gt;)C≡C] (2). On filtration over silica, 2 is readily reprotonated. Complex 1a is inert towards methanol, however, adds diethylamine across the C≡C bond to give the thioacrylamide complex [(CO)&lt;sub&gt;5&lt;/sub&gt;Cr–=C(NMe&lt;sub&gt;2&lt;/sub&gt;)C(H)=C(H)NMe&lt;sub&gt;2&lt;/sub&gt;] (3). Thiourea displaces the thioamide ligand to give [(CO)&lt;sub&gt;5&lt;/sub&gt;Cr–S=C(NH&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;] (4). Complex 1a reacts with half an equivalent of diethylaminopropyne in a three-component coupling to form the homobinuclear complex [(CO)&lt;sub&gt;5&lt;/sub&gt;Cr–=C(NEt&lt;sub&gt;2&lt;/sub&gt;)–C(CH&lt;sub&gt;3&lt;/sub&gt;)=C(H)–C(H)=C(NMe&lt;sub&gt;2&lt;/sub&gt;)–C≡C–C(NMe2)=S–Cr(CO)&lt;sub&gt;5&lt;/sub&gt;] (5) in high yield. The solid state structures of complexes 1a and 5 were established by X-ray structural analyses.</dcterms:abstract>
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