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Volumn 73, Issue 8, 2008, Pages 3197-3204

Regio- and stereoselective lithiation of 2,3-diphenylaziridines: A multinuclear NMR investigation

Author keywords

[No Author keywords available]

Indexed keywords

DIMERS; NUCLEAR MAGNETIC RESONANCE; REGIOSELECTIVITY;

EID: 42149123402     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800069k     Document Type: Article
Times cited : (36)

References (41)
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    • Analogous conclusions have been reported for other lithiated aziridines; see a
    • Analogous conclusions have been reported for other lithiated aziridines; see (a) Haner, R.; Olano, B.; Seebach, D. Helv. Chim. Acta 1987, 70, 1676-1693.
    • (1987) Helv. Chim. Acta , vol.70 , pp. 1676-1693
    • Haner, R.1    Olano, B.2    Seebach, D.3
  • 10
    • 0002191258 scopus 로고
    • Sapse, A.-M, Schleyer, P. von R, Eds, Wiley: New York
    • (c) Boche, G.; Lohrenz, J. C. W.; Opel, A. In Lithium Chemistry; Sapse, A.-M., Schleyer, P. von R., Eds.; Wiley: New York, 1995; p 195.
    • (1995) Lithium Chemistry , pp. 195
    • Boche, G.1    Lohrenz, J.C.W.2    Opel, A.3
  • 18
    • 85161750816 scopus 로고    scopus 로고
    • 7Li HOESY experiments [as reported in (a) Bauer, W. Magn. Reson. Chem. 1996, 34, 532-537;
    • 7Li HOESY experiments [as reported in (a) Bauer, W. Magn. Reson. Chem. 1996, 34, 532-537;
  • 23
    • 42149155362 scopus 로고    scopus 로고
    • α which, however, is similar enough to the signal simulated (Figure 10) using WINDNMR (Reich, H. J
    • α which, however, is similar enough to the signal simulated (Figure 10) using WINDNMR (Reich, H. J. J. Chem. Educ. Software 1996, 3D, 2; http://www.chem.wisc.edu/areas/reich/plt/windnmr.htm).
    • (1996) J. Chem. Educ. Software , vol.3 D , pp. 2
  • 24
    • 0009562713 scopus 로고    scopus 로고
    • 6Li signal was observed obtaining a featureless lump (see the Supporting Information).
    • 6Li signal was observed obtaining a featureless lump (see the Supporting Information).
  • 26
    • 0039758327 scopus 로고    scopus 로고
    • Examples of polyamine solvation and TMEDA effects have been investigated; see a
    • Examples of polyamine solvation and TMEDA effects have been investigated; see (a) Schade, S.; Boche, G. J. Organomet. Chem. 1998, 550, 359-379.
    • (1998) J. Organomet. Chem , vol.550 , pp. 359-379
    • Schade, S.1    Boche, G.2
  • 30
    • 42149101038 scopus 로고    scopus 로고
    • The reaction is extremely slow without TMEDA. All attempts to generate the lithiated intermediate without TMEDA by transmetalation from the corresponding tributyltin aziridine were unsuccessful
    • The reaction is extremely slow without TMEDA. All attempts to generate the lithiated intermediate without TMEDA by transmetalation from the corresponding tributyltin aziridine were unsuccessful.
  • 31
    • 42149108989 scopus 로고    scopus 로고
    • Assuming a cis relationship between the nitrogen lone pair and the Cα-Li bond, the solvent separated ion pair should suffer destabilizing interactions which should favor the isomerization see ref 7
    • α-Li bond, the solvent separated ion pair should suffer destabilizing interactions which should favor the isomerization (see ref 7).
  • 32
    • 33748945005 scopus 로고    scopus 로고
    • For examples of interconversion between the contact ion pair and solvent ion pair, see (a) Reich, H. J, Sikorski, H, Thompson, J. L, Sanders, A. W, Jones, A. C. Org. Lett. 2006, 8, 4003-4006;
    • For examples of interconversion between the contact ion pair and solvent ion pair, see (a) Reich, H. J.; Sikorski, H.; Thompson, J. L.; Sanders, A. W.; Jones, A. C. Org. Lett. 2006, 8, 4003-4006;
  • 36
    • 42149144013 scopus 로고    scopus 로고
    • It has been reported that a crown-ether could also promote, in the flask, the same trans-1-Li to cis-1-Li isomerization see ref 1
    • It has been reported that a crown-ether could also promote, in the flask, the same trans-1-Li to cis-1-Li isomerization (see ref 1).
  • 37
    • 0242475011 scopus 로고    scopus 로고
    • Chemistry, Tetrahedron Symposia-in-Print; Florio, S., Ed
    • For a special issue on aziridinyl anions, see Oxiranyl and Aziridinyl Anions as Reactive Intermediates in
    • (a) For a special issue on aziridinyl anions, see Oxiranyl and Aziridinyl Anions as Reactive Intermediates in Synthetic Organic Chemistry, Tetrahedron Symposia-in-Print; Florio, S., Ed.; Tetrahedron 2003, 59, 9693-9864.
    • (2003) Tetrahedron , vol.59 , pp. 9693-9864
    • Synthetic Organic1
  • 41
    • 42149088792 scopus 로고    scopus 로고
    • The procedure for an experiment with an aziridine/s-BuLi/TMEDA ratio of 1/1.5/1.5 and a sample concentration of 0.06 M is reported. Ratios and concentrations can be changed (0.05-0.2 M).
    • The procedure for an experiment with an aziridine/s-BuLi/TMEDA ratio of 1/1.5/1.5 and a sample concentration of 0.06 M is reported. Ratios and concentrations can be changed (0.05-0.2 M).


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