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

Journal of the American Chemical Society

Volumn 125, Issue 31, 2003, Pages 9300-9301

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

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,2,6,6 TETRAMETHYLPIPERIDINE N OXIDE; ALKENE; CARBENOID; DIVALENT COMPOUND; ELEMENT; GERMANIUM DERIVATIVE; GERMYLENE; NITROXIDE; RADICAL; STANNYLENE; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CALCULATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ELECTRON SPIN RESONANCE; ENERGY TRANSFER; MOLECULAR STABILITY; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0042201925     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0356784     Document Type: Article

References (31)

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3. For recent reviews on divalent species of group 14 elements, see: (a) Gaspar, P. P.; West R. In The Chemistry of Organic Silicon Compounds, Volume 2; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: New York, 1999; Part 3, pp 2463-2568. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Lappert, M. F. Coord. Chem. Rev. 1990, 100, 267. (d) Neumann, W. P. Chem. Rev. 1991, 91, 311. (d) Lappert, M. F. Main Group Met. Chem. 1994, 17, 183. (e) Barrau, J.; Rima, G. Coord. Chem. Rev. 1998, 178-180, 593. (f) Haaf, M.; Schmedake, T. A.; West, R. Acc. Chem. Res. 2000, 33, 704. (g) Gehrhus, B.; Lappert, M. F. J. Organomet. Chem. 2001, 617, 209.
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16. 4Sn: C, 52.62; H, 9.87; N, 3.61%. Found: C, 52.32; H, 9.59; N, 3.44%.
17. max = 54.7°; of 36422 measured reflections, 9211 were independent and 5878 observed with I > 2σ. R1 = 0.053, wR2 (all data) 0.156 for 442 parameters.
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27. 29Si NMR spectra of 5 was unsuccessful because of very low solubility of 8 in organic solvents. For X-ray data, see the Supporting Information.
28. For a recent review on silanone derivatives generated as reactive intermediates, see: Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Silicon Compounds, Volume 2; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: New York, 1999; Part 2, p 1063-1103. See also: Takeda, N.; Tokitoh, N.; Okazaki, R. Chem. Lett. 2000, 244. Khabashesku, V. N.; Kudin, K. M.; Khabashesku, V. N.; Kudin, K. M.; Margrave, J. L.; Fredin, L. J. Organomet. Chem. 2000, 595, 248.
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31. Since the environment around the ring silicon atom in 10 is much more crowded than that around ring germanium in 6, the radical coupling between 10 and TEMPO will be somewhat slower than that between 6 and TEMPO.