Selective Si-C bond cleavage as synthetic entry to a functionalized lithiosilane

Journal of the American Chemical Society

Volumn 127, Issue 22, 2005, Pages 7968-7969

  Strohmann, Carsten ^a   Schildbach, Daniel ^a   Auer, Dominik ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; LITHIOSILANE; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; ORGANIC CHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 20444377349     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050360s     Document Type: Article

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22. This change of color is also known from the reaction of chlorosilanes under similar conditions. There it is evidence for the formation of the corresponding lithiosilane. although it is known that the color is not of the lithiosilane itself, but associated with traces of radical anions formed by side reactions. See ref 5a and references therein.
23. The methoxysilane is available by one-pot reaction from chloro(chloromethyl)methylphenylsilane; cf. Supporting Information.
24. Disilane 7 can also be prepared starting from disilane rac-1. But Si-Si cleavage of rac-1 and reaction with rac-methoxymethylphenyl(piperidinomethyl) silane results in an inseparable product mixture of rac-1 and 7.
25. 2 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 260574.
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30. These isomers include seven pairs of enantiomers and two meso compounds (for a detailed representation of all isomers cf. Supporting Information). A thorough discussion of the occurring structural motifs was given, for example, for 2-lithiobenzylamines, where similar dimeric aggregates are found. See: (a) Reich, H. J.; Goldenberg, W. S.; Gudmundsson, B. O.; Sanders, A. W.; Kulicke, K. J.; Simon, K.; Guzei, I. A. J. Am. Chem. Soc. 2001, 123, 8067 and references therein.
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