Reactions of a Silylyne Complex with Aldehydes: Formation of W−Si−O−C Four-Membered Metallacycles and Their Metathesis-Like Fragmentation

Takashi Yoshimoto, Hisako Hashimoto, Nozomi Takagi, Shigeyoshi Sakaki, Naoki Hayakawa, Tsukasa Matsuo, Hiromi Tobita

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A tungsten silylyne complex having a W≡Si triple bond reacted with two molecules of aldehydes at room temperature to give W−Si−O−C four-membered metallacycles by [2+2] cycloaddition and subsequent formyl hydrogen transfer from one aldehyde molecule to another. Upon heating to 70 °C, the four-membered metallacycles underwent metathesis-like fragmentation cleanly to afford carbyne complexes and “silanoic esters,” in a manner similar to that of metallacyclobutadiene, an intermediate of alkyne metathesis reactions, and dimerization of the latter products gave 1,3-cyclodisiloxanes. The “silanoic ester” was also trapped by pivalaldehyde to give a [2+2] cycloaddition product in high yield.

Original languageEnglish
Pages (from-to)3795-3798
Number of pages4
JournalChemistry - A European Journal
Volume25
Issue number15
DOIs
Publication statusPublished - 2019 Mar 12

Keywords

  • [2+2] cycloaddition
  • aldehyde
  • metathesis-like fragmentation
  • silylyne complex
  • tungsten

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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