Diverse reactions of nitroxide-radical adducts of silylene, germylene, and stannylene

Takeaki Iwamoto, Hidenori Masuda, Shintaro Ishida, Chizuko Kabuto, Mitsuo Kira

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53 Citations (Scopus)


The results of the thermolysis of 1:2 adducts of stable group-14 element divalent compounds [R2M:, R2=1,1,4,4-tetrakis(trimethylsilyl)butane-1,4-diyl; 1b, M=Ge; 1c, M=Sn] to TEMPO radical are discussed in detail. Whereas the thermal reactions of the 1:2 adducts [R2M(OR′)2, R′=2,2,6,6-tetramethylpiperidin-N-yl; 3b, M=Ge; 3c, M=Sn] are understood to proceed by the initial homolysis of an M-O bond to give the corresponding aminoxy-substituted group-14 element radicals [R2(R′O)M; 2b, M=Ge; 2c, M=Sn] and TEMPO, the subsequent reactions of 2b and 2c were remarkably different to each other; 2b favors the N-O bond fission (path b) to give the corresponding germanone, while 2c prefers the M-O bond fission (path a) to give stannylene (1c). In combining with our previous results for aminoxysilyl radical (2a) [R2(R′O)Si], the origin of the remarkable differences in the reactivity among group-14 element radicals 2a-2c is discussed on the basis of the theoretical calculations for model reactions.Improved syntheses of the precursor dichlorogermane and dichlorostannane of germylene (1b) and stannylene (1c), respectively, are described in Section 3.

Original languageEnglish
Pages (from-to)1337-1341
Number of pages5
JournalJournal of Organometallic Chemistry
Issue number8
Publication statusPublished - 2004 Apr 15


  • Bond fission
  • Germanium
  • Nitroxide radical
  • Silicon
  • Stable germylene
  • Stable silylene
  • Stable stannylene
  • Tin
  • X-ray structural analysis

ASJC Scopus subject areas

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


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