Silicon-carbon unsaturated compounds. 77. Thermal behavior of cis- and trans-1-silacyclobut-3-ene formed from pivaloyl[tert-butylbis(trimethylsilyl)] silane and tert-butylacetylene

Akinobu Naka, Hiroyuki Kawasaki, Hiroki Fujimoto, Kazunari Yoshizawa, Mitsuo Ishikawa

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The reaction of tert-butylbis(trimethylsilyl)silyl potassium with pivaloyl chloride gave pivaloyl[tert-butylbis(trimethylsilyl)]silane (1) in 89% yield. The cothermolysis of 1 with tert-butylacetylene at 140 °C for 24 h produced the mixture consisting of cis- and trans-1,2,3-tri(tert-butyl)-2- (trimethylsiloxy)-1-(trimethylsilyl)-1-silacyclobut-3-ene (cis-2 and trans-2) in a ratio of 0.7: 1, in 88% combined yield. The thermolysis of the mixture, cis-2 and trans-2, at 250 °C for 24 h proceeded to give trans-1,2,4-tri(tert- butyl)-1-(trimethylsiloxy)-2-(trimethylsilyl)-1-silacyclobut-3-ene (4) as a single product in 96% yield. Similar treatment of cis- and trans-2 at 190 °C for 15 h afforded silylcyclopropene 3 quantitatively, which underwent further isomerization at 250 °C to give trans-1-silacyclobut-3-ene 4 in quantitative yield.

Original languageEnglish
Pages (from-to)3693-3696
Number of pages4
JournalJournal of Organometallic Chemistry
Volume696
Issue number23
DOIs
Publication statusPublished - Nov 15 2011

All Science Journal Classification (ASJC) codes

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

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