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Synthesis 1992; 1992(6): 577-582
DOI: 10.1055/s-1992-26168
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[1-(Trimethylsiloxy)alkyl]triphenylphosphonium Salts: Syntheses and Utilization. Comparisons with Analogous Pyridinium Salts

Ernst Anders* , Karola Hertlein, Achim Stankowiak, Erhard Irmer
  • *Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestraße 42, D-8520 Erlangen, Germany
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Publication Date:
17 September 2002 (online)

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Three-component reactions with aldehydes, trimethylsilyl trifluoromethanesulfonate or iodide, and triphenylphosphine (TPP) yield the title compounds. The X-ray structure of the cationic part of a representative product, the (4-methylphenyl)[(trimethylsiloxy) methyl]TPP+, shows an interesting lengthening of the P+-C(α) bond compared with reported values for methyl(TPP)+ and benzyl(TPP)+ cations (C(α) represents the P-bonded carbon atom of the various alkyl groups). The behavior of the title compounds towards charged nucleophilic reagents and a powerful electrophile (trifluoromethanesulfonic anhydride) is similar to that of analogous pyridinium salts.