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Volumn 128, Issue 29, 2006, Pages 9355-9360

Structure of n-butyllithium in mixtures of ethers and diamines: Influence of mixed solvation on 1,2-additions to imines

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINES; DIMERS; ETHERS; MIXTURES; REACTION KINETICS; STEREOCHEMISTRY;

EID: 33746369174     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0609654     Document Type: Article
Times cited : (39)

References (77)
  • 2
    • 0004085598 scopus 로고
    • Langer, A. W., Jr., Ed.; American Chemical Society: Washington, D. C.
    • Polyamine-Chelated Alkali Metal Compounds; Langer, A. W., Jr., Ed.; American Chemical Society: Washington, D. C., 1974;
    • (1974) Polyamine-Chelated Alkali Metal Compounds
  • 8
    • 33746383574 scopus 로고    scopus 로고
    • U.S. Patent 3,451,988, 1960
    • The first report of a polyamine-modified organolithium reaction appeared in 1960: Langer, A. W., Jr. U.S. Patent 3,451,988, 1960.
    • Langer Jr., A.W.1
  • 9
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, Y., Eds; Springer-Verlag: Heidelberg ; Chapter 26.2
    • Reviews describing some organolithium chemistry of imines: Denmark, S. E.; Nicaise. O. I.-C. In Comprehensive Asymmetric Catalvsis; Jacobsen, E. N., Pfaltz, A., Yamamoto, Y., Eds; Springer-Verlag: Heidelberg, 1999; Chapter 26.2;
    • (1999) Comprehensive Asymmetric Catalvsis
    • Denmark, S.E.1    Nicaise, O.I.-C.2
  • 12
    • 0003417469 scopus 로고
    • Trost, B. M., Fleming, I., Eds; Pergamon: Oxford : Chapter 1.12
    • Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, 1991: Chapter 1.12;
    • (1991) Comprehensive Organic Synthesis
    • Volkmann, R.A.1
  • 29
  • 31
  • 49
    • 0032875055 scopus 로고    scopus 로고
    • Equation Presented
    • 6Li resonances (1:1) consistent with mixed dimer i, which is akin to that fully characterized previously: Arvidsson, P. I.; Hilmersson, G.; Davidsson, O. Chem. Eur. J. 1999, 5, 2348. (Equation Presented)
    • (1999) Chem. Eur. J. , vol.5 , pp. 2348
    • Arvidsson, P.I.1    Hilmersson, G.2    Davidsson, O.3
  • 50
    • 33746330852 scopus 로고    scopus 로고
    • note
    • n-BuLi concentration refers to the total concentration (normality). TMCDA concentration refers to the concentration of the free (uncomplexed) ligand.
  • 51
    • 33746324350 scopus 로고    scopus 로고
    • note
    • The five-point curves in Figure 2 reveal inverse first orders, but with considerable error. The cited order of -1.0 derives from a more fully developed data set found in Supporting Information.
  • 54
    • 30244499949 scopus 로고
    • For the proper treatment of statistical factors, see: Benson, S. W. J. Am. Chem. Soc. 1958, 80, 5151;
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 5151
    • Benson, S.W.1
  • 55
    • 0000796832 scopus 로고
    • For additional leading references to statistical contributions in "redistribution reactions," see: Fay, R. C.; Lowry, R. N. Inorg. Chem. 1974, 13, 1309.
    • (1974) Inorg. Chem. , vol.13 , pp. 1309
    • Fay, R.C.1    Lowry, R.N.2
  • 56
    • 33746330220 scopus 로고    scopus 로고
    • note
    • For studies of TMCDA-solvated lithium salts, see ref 9 and references therein.
  • 59
    • 33746352170 scopus 로고    scopus 로고
    • note
    • We routinely find that calculated structures of congested systems backed with strong experimental support are challenging to minimize and often afford distortions (elongated bonds) that may or may not represent an adequate simulation.
  • 63
    • 0344443341 scopus 로고    scopus 로고
    • For additional leading references to spectroscopic, crystallographic, and kinetic evidence of open dimers, see: Zhao, P.; Collum, D. B. J. Am. Chem. Soc. 2003, 125, 14411:
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14411
    • Zhao, P.1    Collum, D.B.2
  • 69
    • 0001542058 scopus 로고
    • For an early report of a tetramer-based reaction requiring the dissociation of a coordinating ligand, see: Bartlett, P. D.; Goebel, C. V.; Weber, W. P. J. Am. Chem. Soc. 1969, 91, 7425.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 7425
    • Bartlett, P.D.1    Goebel, C.V.2    Weber, W.P.3
  • 71
    • 0035897440 scopus 로고    scopus 로고
    • For a structurally related triple ion bearing a TMEDA-chelated internal lithium, see: Bildmann, U. J.; Muller, G. Organometallics 2001, 20, 1689.
    • (2001) Organometallics , vol.20 , pp. 1689
    • Bildmann, U.J.1    Muller, G.2
  • 72
    • 0036284512 scopus 로고    scopus 로고
    • 2 moiety. Differences between TMEDA and TMCDA as ligands have also been attributed to the fixed bite-angle of TMCDA: Heuger, G.; Kalsow, S.; Göttlich, R. Eur. J. Org. Chem. 2002, 1848.
    • (2002) Eur. J. Org. Chem. , pp. 1848
    • Heuger, G.1    Kalsow, S.2    Göttlich, R.3
  • 73
    • 33746338690 scopus 로고    scopus 로고
    • unpublished
    • We have found in a number of computational studies that ion pair separation in such destabilized lithium salts is inordinately costly. Ramirez A.; Collum, D. B., unpublished.
    • Ramirez, A.1    Collum, D.B.2
  • 74
    • 33746339320 scopus 로고    scopus 로고
    • note
    • 5 Preliminary data using TMCDA appear to be consistent with an analogous scenario, but detailed rate studies were not completed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.