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Volumn 70, Issue 15, 2005, Pages 5964-5973

Generalized synthesis and physical properties of dialkoxy disulfides

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL BONDS; COALESCENCE; PYROLYSIS; SYNTHESIS (CHEMICAL);

EID: 22244440748     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050574s     Document Type: Article
Times cited : (22)

References (134)
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  • 25
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    • Jackman, L. M., Cotton, F. A., Eds.; Academic Press: New York
    • For a review on rotation about single bonds, see: Sternhell, S. Dynamic Nuclear Magnetic Resonance Spectroscopy; Jackman, L. M., Cotton, F. A., Eds.; Academic Press: New York, 1975; Vol. 6.
    • (1975) Dynamic Nuclear Magnetic Resonance Spectroscopy , vol.6
    • Sternhell, S.1
  • 46
    • 0001077957 scopus 로고
    • Some have argued that the high observed barrier in amides is due to the inherent preference for nitrogen planarity, resulting in its effective increase in electronegativity and thus better ability to stabilize itself. See for instance: Wiberg, K. B.; Breneman, C. M. J. Am. Chem. Soc. 1992, 114, 831.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 831
    • Wiberg, K.B.1    Breneman, C.M.2
  • 65
    • 0004065524 scopus 로고
    • Academic Press: Toronto
    • For an excellent reference on DNMR spectroscopy, see: Sandström, J. Dynamic NMR Spectroscopy; Academic Press: Toronto, 1982.
    • (1982) Dynamic NMR Spectroscopy
    • Sandström, J.1
  • 68
    • 3242690262 scopus 로고
    • Meuwsen, A. Ber. 1936, 69, 935.
    • (1936) Ber. , vol.69 , pp. 935
    • Meuwsen, A.1
  • 79
    • 20444501674 scopus 로고
    • 3) for a series of 2-alkoxy-3-halobutanes and 2-acetoxy-3-halobutanes. See: Wang, C. Y.; Bushweller, C. H. J. Am. Chem. Soc. 1977, 99, 313.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 313
    • Wang, C.Y.1    Bushweller, C.H.2
  • 81
    • 0001402646 scopus 로고
    • Some have attributed the observed solvent effect in the rotation about the C-N amide bond to internal pressure and the increased volume requirements of the transition state structure in comparison to the ground-state structure. See for instance: Suarez, C.; Lemaster, C. B.; Lemaster, C. L.; Tafazzoli, M.; True, N. S. J. Phys. Chem. 1990, 94, 6679. It should be noted that in the case of dialkoxy disulfides, the transition state does not demand greater steric requirements compared to the ground state. Thus, any increase in the barrier in the liquid phase compared to the gas-phase cannot be due to this reasoning.
    • (1990) J. Phys. Chem. , vol.94 , pp. 6679
    • Suarez, C.1    Lemaster, C.B.2    Lemaster, C.L.3    Tafazzoli, M.4    True, N.S.5
  • 93
    • 0000598486 scopus 로고    scopus 로고
    • and references therein
    • For a review on methodology that gives estimates and trends concerning torsional entropy about single bonds, see: Mammen, M.; Shakhnovich, E. I.; Whitesides, G. M. J. Org. Chem. 1998, 63, 3168 and references therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 3168
    • Mammen, M.1    Shakhnovich, E.I.2    Whitesides, G.M.3
  • 94
    • 0033617432 scopus 로고    scopus 로고
    • For a commentary on the definition of torsional entropy, see: Ercolani, G. J. Org. Chem. 1999, 64, 3350.
    • (1999) J. Org. Chem. , vol.64 , pp. 3350
    • Ercolani, G.1
  • 96
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    • note
    • 2 value for the linear fits was ca. 0.97.
  • 104
    • 22244492050 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy.
  • 126
    • 22244479747 scopus 로고    scopus 로고
    • note
    • Formation of sulfenyl radical 13 via homolysis of the S-S bond cannot be ruled out.
  • 132
    • 22244479407 scopus 로고    scopus 로고
    • note
    • The three electrons would be placed in a new set of π and π* orbitals.
    • π and π* Orbitals.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.