Synthesis and copper-catalyzed reactions of α-metalated diazocarbonyl compounds

O. A. Kruglaya, I. B. Fedot'eva, B. V. Fedot'ev, I. D. Kalikhman, E. I. Brodskaya, N. S. Vyazankin

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


Monogermylated ketenes, R(Et3Ge)CCO, have been prepared by the Wolff rearrangement of carbenoids, Et3GeC̈COR, generated by the copper-catalyzed decomposition of the corresponding α-(triethylgermyl)diazo ketones in hexane. In contrast, triethylsilyldiazoacetone decomposes over copper by another reaction scheme to give, unexpectedly 1,1-diethyl-3,5-dimethyl-2-oxa-1-sila-3-cyclopentene. The copper-catalyzed interaction of Et3MC(N2)COOEt (M = Si, Ge, Sn) with bis(triethylsilyl)- or bis(triethylgermyl)-mercury results in high yield of the corresponding bimetalated ketenes, Et3M(Et3M′)CCO, where M and M′ are Si, Ge or Sn. The first step in this interaction probably involves the insertion of the carbenoid, Et3MC̈CO2Et, into the Group IV element-mercury bond. The general procedure for the preparation of α-metalated diazocarbonyl compounds via readily available bis(triethylsilyl)- and bis(triethylgermyl)-mercury is described.

Original languageEnglish
Pages (from-to)155-164
Number of pages10
JournalJournal of Organometallic Chemistry
Issue number2
StatePublished - 13 Dec 1977
Externally publishedYes

ASJC Scopus subject areas

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


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