A planar silacyclobutane, 1,1-(rac-1,1′-bi-2-naphthoxy)-1- silacyclobutane and its unusual reaction with bis(1,5-cyclooctadiene)platinum(0)

Rajsapan Jain, Andrew P.J. Brunskill, John B. Sheridan, Roger A. Lalancette

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The synthesis, characterization and X-ray crystal structure of 1,1-(rac-1,1′-bi-2-naphthoxy)-1-silacyclobutane (1) are reported and reveal an unusual planar conformation with a Si-βC distance of 2.302 (5) Å. Reaction of 1 with either stoichiometric or catalytic amounts of bis(1,5-cyclooctadiene)platinum(0) {Pt(cod)2} gave 1,1′-bi-2-naphthol (BINOL), rather than the expected insertion products or polymer. A mechanism is proposed based on insertion of the Pt(cod) into 1 followed by hydride transfers via the Pt center to the 1,1′-bi-2-naphthoxy group. Anionic ring-opening polymerization of 1 is also reported and gave the poly(carbosilane) (4).

Original languageEnglish (US)
Pages (from-to)2272-2277
Number of pages6
JournalJournal of Organometallic Chemistry
Volume690
Issue number9
DOIs
StatePublished - Apr 29 2005

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Keywords

  • Platinum-catalyzed
  • Silacyclobutane

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