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Substituted silastannatetrahydro-s-indacenes as cyclopentadienyl transfer agents in the synthesis of silanediyl bridged zirconocene complexes

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1996

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Hüttenhofer, Mario
Prosenc, Marc-Heinrich
Rief, Ursula
Schaper, Frank

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http://nbn-resolving.de/urn:nbn:de:bsz:352-237606
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https://doi.org/10.1021/om960305f
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Organometallics. 1996, 15(22), pp. 4816-4822. ISSN 0276-7333. eISSN 1520-6041. Available under: doi: 10.1021/om960305f

Zusammenfassung

The substituted silastannatetrahydro-s-indacenes meso-Me2Si(t-BuC5H3)2SnMe2, meso-Me2Si(Me2C5H2)2SnMe2, and meso-Me2Si(Me-i-PrC5H2)2SnMe2, prepared from the corresponding silanediyl-bridged dicyclopentadienide dilithium salts by reaction with Me2SnCl2, were structurally characterized by X-ray diffraction and by 1H-NMR in solution. These cyclic stannanediyl compounds react with ZrCl4 to give selectively the meso diastereomers of the ansa-zirconocene complexes Me2Si(3-t-BuC5H3)2ZrCl2, Me2Si(2,4-Me2C5H2)2ZrCl2, and Me2Si(2-Me-4-i-PrC5H2)2ZrCl2, respectively. Reaction of Me2Si(2-Me-4-t-BuC5H2 - Li+)2 with Me2SnCl2 gives, instead of Me2Si(Me-t-BuC5H2)2SnMe2, the distannyl derivative Me2Si(2-Me-4-t-BuC5H2-1-SnMe2Cl)2. This compound reacts with ZrCl4 to give a 1:1 mixture of the rac and meso isomers of Me2Si(2-Me-4-t-BuC5H2)2ZrCl2. Ring-opened, racemic distannyl compounds are formed also from meso-Me2Si(t-BuC5H3)2SnMe2, meso-Me2Si(Me2C5H2)2SnMe2, and meso-Me2Si(Me-i-PrC5H2)2SnMe2 with excess Me2SnCl2. Competition between Me2SnCl2 and Zr centers for reaction with stannylcyclopentadiene units appears to limit the overall stereoselectivity of the ansa-zirconocene complex formation.

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ISO 690HÜTTENHOFER, Mario, Marc-Heinrich PROSENC, Ursula RIEF, Frank SCHAPER, Hans-Herbert BRINTZINGER, 1996. Substituted silastannatetrahydro-s-indacenes as cyclopentadienyl transfer agents in the synthesis of silanediyl bridged zirconocene complexes. In: Organometallics. 1996, 15(22), pp. 4816-4822. ISSN 0276-7333. eISSN 1520-6041. Available under: doi: 10.1021/om960305f
BibTex
@article{Huttenhofer1996Subst-23760,
  year={1996},
  doi={10.1021/om960305f},
  title={Substituted silastannatetrahydro-s-indacenes as cyclopentadienyl transfer agents in the synthesis of silanediyl bridged zirconocene complexes},
  number={22},
  volume={15},
  issn={0276-7333},
  journal={Organometallics},
  pages={4816--4822},
  author={Hüttenhofer, Mario and Prosenc, Marc-Heinrich and Rief, Ursula and Schaper, Frank and Brintzinger, Hans-Herbert}
}
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    <dcterms:abstract xml:lang="eng">The substituted silastannatetrahydro-s-indacenes meso-Me&lt;sub&gt;2&lt;/sub&gt;Si(t-BuC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;3&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;SnMe&lt;sub&gt;2&lt;/sub&gt;, meso-Me&lt;sub&gt;2&lt;/sub&gt;Si(Me&lt;sub&gt;2&lt;/sub&gt;C&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;SnMe&lt;sub&gt;2&lt;/sub&gt;, and meso-Me&lt;sub&gt;2&lt;/sub&gt;Si(Me-i-PrC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;SnMe&lt;sub&gt;2&lt;/sub&gt;, prepared from the corresponding silanediyl-bridged dicyclopentadienide dilithium salts by reaction with Me&lt;sub&gt;2&lt;/sub&gt;SnCl&lt;sub&gt;2&lt;/sub&gt;, were structurally characterized by X-ray diffraction and by &lt;sup&gt;1&lt;/sup&gt;H-NMR in solution. These cyclic stannanediyl compounds react with ZrCl&lt;sub&gt;4&lt;/sub&gt; to give selectively the meso diastereomers of the ansa-zirconocene complexes Me&lt;sub&gt;2&lt;/sub&gt;Si(3-t-BuC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;3&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;ZrCl&lt;sub&gt;2&lt;/sub&gt;, Me&lt;sub&gt;2&lt;/sub&gt;Si(2,4-Me&lt;sub&gt;2&lt;/sub&gt;C&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;ZrCl&lt;sub&gt;2&lt;/sub&gt;, and Me&lt;sub&gt;2&lt;/sub&gt;Si(2-Me-4-i-PrC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;ZrCl&lt;sub&gt;2&lt;/sub&gt;, respectively. Reaction of Me&lt;sub&gt;2&lt;/sub&gt;Si(2-Me-4-t-BuC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt; &lt;sup&gt;-&lt;/sup&gt; Li&lt;sup&gt;+&lt;/sup&gt;)&lt;sub&gt;2&lt;/sub&gt; with Me&lt;sub&gt;2&lt;/sub&gt;SnCl&lt;sub&gt;2&lt;/sub&gt; gives, instead of Me&lt;sub&gt;2&lt;/sub&gt;Si(Me-t-BuC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;SnMe&lt;sub&gt;2&lt;/sub&gt;, the distannyl derivative Me&lt;sub&gt;2&lt;/sub&gt;Si(2-Me-4-t-BuC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt;-1-SnMe&lt;sub&gt;2&lt;/sub&gt;Cl)&lt;sub&gt;2&lt;/sub&gt;. This compound reacts with ZrCl&lt;sub&gt;4&lt;/sub&gt; to give a 1:1 mixture of the rac and meso isomers of Me&lt;sub&gt;2&lt;/sub&gt;Si(2-Me-4-t-BuC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;ZrCl&lt;sub&gt;2&lt;/sub&gt;. Ring-opened, racemic distannyl compounds are formed also from meso-Me&lt;sub&gt;2&lt;/sub&gt;Si(t-BuC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;3&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;SnMe&lt;sub&gt;2&lt;/sub&gt;, meso-Me&lt;sub&gt;2&lt;/sub&gt;Si(Me&lt;sub&gt;2&lt;/sub&gt;C&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;SnMe&lt;sub&gt;2&lt;/sub&gt;, and meso-Me&lt;sub&gt;2&lt;/sub&gt;Si(Me-i-PrC&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;SnMe&lt;sub&gt;2&lt;/sub&gt; with excess Me&lt;sub&gt;2&lt;/sub&gt;SnCl&lt;sub&gt;2&lt;/sub&gt;. Competition between Me&lt;sub&gt;2&lt;/sub&gt;SnCl&lt;sub&gt;2&lt;/sub&gt; and Zr centers for reaction with stannylcyclopentadiene units appears to limit the overall stereoselectivity of the ansa-zirconocene complex formation.</dcterms:abstract>
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