Structure and natural bond orbital analysis of oxiranes substituted with a group 14 element. A comment of Sn2 regioselectivity

Chemistry Letters

Volumn , Issue 5, 1999, Pages 409-410

  Ikeno, Taketo ^a   Harada, Jun ^a   Tomoda, Shuji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033241992     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.409     Document Type: Article

References (23)

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4. For review, see P. F. Hudrlik and A. M. Hudrlik, in "Advances in Silicon Chemistry," ed by G. L. Larson, JAI Press, Greenwich, CT (1993), Vol. 2, p 1; E. Colvin, in "Silicon in Organic Synthesis", Butterworth, London (1981).
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9. Six X-ray structures of α,β-epoxysilanes have been reported, but systematic analysis of C-O bond lengths has not been done. U. Siriwardane, S. S. C. Chu, and J. D. Buynak, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 45, 531 (1989); G. A. Molander and K. Mautner, J. Org. Chem., 54, 4042 (1989); K. Yamamoto, Y. Kawanami, and M. Miyazawa, J. Chem. Soc., Chem. Commun., 1993, 436; T. Kawai, M. Isobe, and S. C. Peters, Aust. J. Chem., 48, 115 (1995); M. M. Kabat, J. Org. Chem., 60, 1823 (1995). D. M. Hodgson, P. J. Comina, and M. G. B. Drew, J. Chem. Soc., Perkin Trans I, 1997, 2279.
10. Six X-ray structures of α,β-epoxysilanes have been reported, but systematic analysis of C-O bond lengths has not been done. U. Siriwardane, S. S. C. Chu, and J. D. Buynak, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 45, 531 (1989); G. A. Molander and K. Mautner, J. Org. Chem., 54, 4042 (1989); K. Yamamoto, Y. Kawanami, and M. Miyazawa, J. Chem. Soc., Chem. Commun., 1993, 436; T. Kawai, M. Isobe, and S. C. Peters, Aust. J. Chem., 48, 115 (1995); M. M. Kabat, J. Org. Chem., 60, 1823 (1995). D. M. Hodgson, P. J. Comina, and M. G. B. Drew, J. Chem. Soc., Perkin Trans I, 1997, 2279.
11. Six X-ray structures of α,β-epoxysilanes have been reported, but systematic analysis of C-O bond lengths has not been done. U. Siriwardane, S. S. C. Chu, and J. D. Buynak, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 45, 531 (1989); G. A. Molander and K. Mautner, J. Org. Chem., 54, 4042 (1989); K. Yamamoto, Y. Kawanami, and M. Miyazawa, J. Chem. Soc., Chem. Commun., 1993, 436; T. Kawai, M. Isobe, and S. C. Peters, Aust. J. Chem., 48, 115 (1995); M. M. Kabat, J. Org. Chem., 60, 1823 (1995). D. M. Hodgson, P. J. Comina, and M. G. B. Drew, J. Chem. Soc., Perkin Trans I, 1997, 2279.
12. Six X-ray structures of α,β-epoxysilanes have been reported, but systematic analysis of C-O bond lengths has not been done. U. Siriwardane, S. S. C. Chu, and J. D. Buynak, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 45, 531 (1989); G. A. Molander and K. Mautner, J. Org. Chem., 54, 4042 (1989); K. Yamamoto, Y. Kawanami, and M. Miyazawa, J. Chem. Soc., Chem. Commun., 1993, 436; T. Kawai, M. Isobe, and S. C. Peters, Aust. J. Chem., 48, 115 (1995); M. M. Kabat, J. Org. Chem., 60, 1823 (1995). D. M. Hodgson, P. J. Comina, and M. G. B. Drew, J. Chem. Soc., Perkin Trans I, 1997, 2279.
13. Six X-ray structures of α,β-epoxysilanes have been reported, but systematic analysis of C-O bond lengths has not been done. U. Siriwardane, S. S. C. Chu, and J. D. Buynak, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 45, 531 (1989); G. A. Molander and K. Mautner, J. Org. Chem., 54, 4042 (1989); K. Yamamoto, Y. Kawanami, and M. Miyazawa, J. Chem. Soc., Chem. Commun., 1993, 436; T. Kawai, M. Isobe, and S. C. Peters, Aust. J. Chem., 48, 115 (1995); M. M. Kabat, J. Org. Chem., 60, 1823 (1995). D. M. Hodgson, P. J. Comina, and M. G. B. Drew, J. Chem. Soc., Perkin Trans I, 1997, 2279.
14. Six X-ray structures of α,β-epoxysilanes have been reported, but systematic analysis of C-O bond lengths has not been done. U. Siriwardane, S. S. C. Chu, and J. D. Buynak, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 45, 531 (1989); G. A. Molander and K. Mautner, J. Org. Chem., 54, 4042 (1989); K. Yamamoto, Y. Kawanami, and M. Miyazawa, J. Chem. Soc., Chem. Commun., 1993, 436; T. Kawai, M. Isobe, and S. C. Peters, Aust. J. Chem., 48, 115 (1995); M. M. Kabat, J. Org. Chem., 60, 1823 (1995). D. M. Hodgson, P. J. Comina, and M. G. B. Drew, J. Chem. Soc., Perkin Trans I, 1997, 2279.
15. Triphenylmethyloxirane (3) was prepared from triphenylvinylmetnane by treatment with dimetliyldioxirane in 82% yield.
16. -3, T = 90 K, R1(wR2)=0.025 (0.057), number of unique reflections 7258.
17. All the calculations were performed using Gaussian 94. (Revision D. 1): Gaussian, Inc., Pittsburgh PA, (1995).
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20. Reaction rate was measured at pH 7 by titration with HBr solution according to the literature; P. L. Nichols Jr. and J. Ingham, J. Am. Chem. Soc., 77, 6547 (1955); W. L. Petty and P. L. Nichols Jr., J. Am. Chem. Soc., 76, 4385 (1954).
21. Reaction rate was measured at pH 7 by titration with HBr solution according to the literature; P. L. Nichols Jr. and J. Ingham, J. Am. Chem. Soc., 77, 6547 (1955); W. L. Petty and P. L. Nichols Jr., J. Am. Chem. Soc., 76, 4385 (1954).
22. T. A. Albright, J. K. Burdett, and M.-H. Whangbo, "Orbital Interactions in Chemistry," Wiley, New York (1985); I. Fleming, "Frontier Orbitals and Organic Chemical Reactions," Wiley, London (1976).
23. T. A. Albright, J. K. Burdett, and M.-H. Whangbo, "Orbital Interactions in Chemistry," Wiley, New York (1985); I. Fleming, "Frontier Orbitals and Organic Chemical Reactions," Wiley, London (1976).