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Volumn 44, Issue 21, 2005, Pages 3275-3279

"On water": Unique reactivity of organic compounds in aqueous suspension

Author keywords

Click chemistry; Cycloaddition; Interfaces; Rearrangement; Water chemistry

Indexed keywords

ORGANIC COMPOUNDS; ORGANIC SOLVENTS; SOLUBILITY; SUSPENSIONS (FLUIDS); WATER;

EID: 20344388819     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462883     Document Type: Article
Times cited : (1596)

References (58)
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    • b) "Structure and Reactivity in Aqueous Solution", R. Breslow, ACS Symp. Ser. 1994, 568, 291.
    • (1994) ACS Symp. Ser. , vol.568 , pp. 291
    • Breslow, R.1
  • 13
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    • NIST Standard Reference Database Number 69, March 2003, National Institute of Standards and Technology, Gaithersburg MD, 20899
    • -3 K, water has an unusually high heat capacity for a liquid; see: NIST Chemistry WebBook (Eds.: P. J. Linstrom, W. G. Mallard), NIST Standard Reference Database Number 69, March 2003, National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.gov).
    • NIST Chemistry WebBook
    • Linstrom, P.J.1    Mallard, W.G.2
  • 16
    • 20344376081 scopus 로고    scopus 로고
    • note
    • The amount of water used can be chosen to best balance/control the exothermicity of the reaction, as the resulting increase in total reaction volume does not constitute dilution of the reaction zone.
  • 17
    • 0344980985 scopus 로고
    • For an example of solvent effect on the cycloaddition of quadricyclane with azodicarbonyl compounds, see: M. E. Landis, J. C. Mitchell, J. Org. Chem. 1979, 44, 2288.
    • (1979) J. Org. Chem. , vol.44 , pp. 2288
    • Landis, M.E.1    Mitchell, J.C.2
  • 19
    • 20344402204 scopus 로고
    • For the only reported example, to our knowledge, of the accelerating influence of water on the reactions of azodicarboxylates, see: L. E. Gast, E. W. Bell, H. M. Teeter, J. Am. Oil Chem. Soc. 1956, 33, 278.
    • (1956) J. Am. Oil Chem. Soc. , vol.33 , pp. 278
    • Gast, L.E.1    Bell, E.W.2    Teeter, H.M.3
  • 21
    • 33751386424 scopus 로고
    • For Lewis acid mediated ene reactions of azodicarboxylates at -60°C, see: M. A. Brimble, C. H. Heathcock, J. Org. Chem. 1993, 58, 5261.
    • (1993) J. Org. Chem. , vol.58 , pp. 5261
    • Brimble, M.A.1    Heathcock, C.H.2
  • 26
    • 0041818406 scopus 로고    scopus 로고
    • For an excellent recent review of the role of hydrophobic effects on reactivity, see: S. Otto, J. B. F. N. Engberts, Org. Biomol. Chem. 2003, 1, 2809.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 2809
    • Otto, S.1    Engberts, J.B.F.N.2
  • 30
    • 20344390169 scopus 로고    scopus 로고
    • note
    • As both starting materials and the product are oils, the neat reaction is not prone to physical "mixing" issues, which can arise when one of the reactants is a solid. Even when mixing is not an issue, we have encountered a few cases where the reactions "on water" are two- to threefold faster than the corresponding neat reaction, although the example shown here is typical.
  • 38
    • 20344394027 scopus 로고    scopus 로고
    • See Ref. [25]
    • Grieco subsequently reported that the rearrangement of the same methyl ester in aqueous suspension was qualitatively comparable in rate and efficiency to that of the carboxylate salt in homogeneous solution. See Ref. [25].
  • 44
    • 0010421423 scopus 로고
    • Structure and Reactivity in Aqueous Solution: Characterization of Chemical and Biological Systems
    • "Structure and Reactivity in Aqueous Solution: Characterization of Chemical and Biological Systems", J. J. Gajewski, N. L. Brichford, ACS Symp. Ser. 1994, 568, 229.
    • (1994) ACS Symp. Ser. , vol.568 , pp. 229
    • Gajewski, J.J.1    Brichford, N.L.2
  • 47
    • 0010421423 scopus 로고
    • Structure and Reactivity in Aqueous Solution
    • b) "Structure and Reactivity in Aqueous Solution", W. Blokzijl, J. B. F. N. Engberts, ACS Symp. Ser. 1994, 568, 303.
    • (1994) ACS Symp. Ser. , vol.568 , pp. 303
    • Blokzijl, W.1    Engberts, J.B.F.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.