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Volumn 62, Issue 14, 1997, Pages 4737-4745

Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates

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EID: 0001323039     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970263k     Document Type: Article
Times cited : (19)

References (64)
  • 1
    • 0000979520 scopus 로고    scopus 로고
    • Hoz has argued that orbital effects and ground state destabilization contribute to rate accelerations observed in reactions of strained rings: (a) Sella, A.; Basch, H.; Hoz, S. J. Am. Chem. Soc. 1996, 118, 416-420. (b) Sella, A.; Basch, H.; Hoz, S. Tetrahedron Lett. 1996, 37, 5573-5576.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 416-420
    • Sella, A.1    Basch, H.2    Hoz, S.3
  • 2
    • 0030605831 scopus 로고    scopus 로고
    • Hoz has argued that orbital effects and ground state destabilization contribute to rate accelerations observed in reactions of strained rings: (a) Sella, A.; Basch, H.; Hoz, S. J. Am. Chem. Soc. 1996, 118, 416-420. (b) Sella, A.; Basch, H.; Hoz, S. Tetrahedron Lett. 1996, 37, 5573-5576.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5573-5576
    • Sella, A.1    Basch, H.2    Hoz, S.3
  • 4
    • 85013550214 scopus 로고
    • Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon: New York
    • Padwa, A.; Murphree, S. S. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon: New York, 1994; Vol. 6; pp 56-73.
    • (1994) Progress in Heterocyclic Chemistry , vol.6 , pp. 56-73
    • Padwa, A.1    Murphree, S.S.2
  • 18
    • 0038092166 scopus 로고
    • The ring strain of the parent silirane has been calculated to be 44 kcal/mol: Gordon, M. S.; Nelson, W. Organometallics 1995, 14, 1067-1069.
    • (1995) Organometallics , vol.14 , pp. 1067-1069
    • Gordon, M.S.1    Nelson, W.2
  • 22
    • 1542689692 scopus 로고    scopus 로고
    • Fleming has provided insightful analysis of our data: Fleming, I. Chemtracts-Org. Chem. 1996, 9, 121-125.
    • (1996) Chemtracts-Org. Chem. , vol.9 , pp. 121-125
    • Fleming, I.1
  • 28
    • 0000936121 scopus 로고    scopus 로고
    • Ring opening of postulated silacyclopropene intermediates by MeOH, MeCHO, and acetone has been reported: Lee, S. T.; Baek, E. K.; Shim, S. C. Organometallics 1996, 15, 2182-2184.
    • (1996) Organometallics , vol.15 , pp. 2182-2184
    • Lee, S.T.1    Baek, E.K.2    Shim, S.C.3
  • 30
    • 85033136122 scopus 로고    scopus 로고
    • Thermal deuteriomethanolysis proceeded with the same stereochemical outcome, albeit with extensive decomposition
    • Thermal deuteriomethanolysis proceeded with the same stereochemical outcome, albeit with extensive decomposition.
  • 31
    • 0007623379 scopus 로고
    • For example, the 3-deuterio-2-butanols are known: Kabalka, G. W.; Bowman, N. S. J. Org. Chem. 1973, 38, 1607-1608.
    • (1973) J. Org. Chem. , vol.38 , pp. 1607-1608
    • Kabalka, G.W.1    Bowman, N.S.2
  • 32
  • 33
    • 85033153063 scopus 로고    scopus 로고
    • note
    • Control experiments indicate that the products are formed kinetically and that no isomerization of the silirane occurred during either the thermal or catalyzed insertions.
  • 47
    • 85033141845 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of the major isomers 20a of the two substituted systems compared to that of 10a. Because the reactions were low-yielding, no further attempts were made to prove the stereochemistry.
  • 48
    • 85033134831 scopus 로고    scopus 로고
    • The details are provided as Supporting Information
    • The details are provided as Supporting Information.
  • 53
    • 85033139031 scopus 로고    scopus 로고
    • note
    • Further confirmation of the stereochemistry of 27 was obtained by reductive amination of the corresponding primary diamine with benzaldehyde.
  • 54
    • 0001671575 scopus 로고
    • For reactions of silylenes with imines, see: (a) Weidenbruch, M.; Piel, H.; Peters, K.; von Schnering, H. G. Organometallics 1993, 12, 2881-2882. (b) Belzner, J.; Ihmels, H.; Pauletto, L.; Noltemeyer, M. J. Org. Chem. 1996, 61, 3315-3319.
    • (1993) Organometallics , vol.12 , pp. 2881-2882
    • Weidenbruch, M.1    Piel, H.2    Peters, K.3    Von Schnering, H.G.4
  • 55
    • 0006298183 scopus 로고    scopus 로고
    • For reactions of silylenes with imines, see: (a) Weidenbruch, M.; Piel, H.; Peters, K.; von Schnering, H. G. Organometallics 1993, 12, 2881-2882. (b) Belzner, J.; Ihmels, H.; Pauletto, L.; Noltemeyer, M. J. Org. Chem. 1996, 61, 3315-3319.
    • (1996) J. Org. Chem. , vol.61 , pp. 3315-3319
    • Belzner, J.1    Ihmels, H.2    Pauletto, L.3    Noltemeyer, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.