Addition of stable nitroxide radical to stable divalent compounds of heavier group 14 elements

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

Research output: Contribution to journalArticlepeer-review

72 Citations (Scopus)

Abstract

The reactions of stable cyclic dialkylgermylene 2 and dialkylstannylene 3 with 2,2,6,6-tetramethylpiperidinyl-1-oxy (TEMPO) radical (2 equiv) gave the corresponding 1:2 adducts 4 and 5, respectively, which were characterized by NMR, MS, and X-ray analyses. The kinetics of the stepwise addition of two TEMPO molecules to germylene 2 revealed that the initial addition of TEMPO to 2 was 1010 times slower than the second TEMPO addition to the resulting germyl radical. The origin of the rate difference was discussed on the basis of the qualitative perturbation theory. In contrast to the reactions of 2 and 3, the reaction of dialkylsilylene 1 with TEMPO gave an interesting 1,3-dioxadisiletane derivative.

Original languageEnglish
Pages (from-to)9300-9301
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number31
DOIs
Publication statusPublished - 2003 Aug 6

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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