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Volumn 22, Issue 17, 2003, Pages 3374-3381

Catalytic olefin cyclopropanation using μ-oxo-bis[(salen)iron(III)] complexes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST LOADING;

EID: 0041877226     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020959q     Document Type: Article
Times cited : (61)

References (47)
  • 1
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    • Salaun, J. Chem. Rev. 1989, 89, 1247-1270.
    • (1989) Chem. Rev. , vol.89 , pp. 1247-1270
    • Salaun, J.1
  • 25
    • 0043279025 scopus 로고    scopus 로고
    • note
    • -] tetradentate bis(Schiff base) ligands. "salen" itself is often used to indicate a member of this class, that which is derived from ethylenediamine. However, for ease of nomenclature in the remainder of this article the term salen will also be used to describe the general class of bis(salicylaldimine) ligands and their complexes.
  • 31
    • 0041775787 scopus 로고
    • EDA is known to thermally add to ethylenic linkages to form five-membered pyrazoline carboxylic esters via 1,3-dipolar cycloadditions. (See: Drake, N. L.; Sweeney, T. R. J. Org. Chem. 1948, 11, 67-74.1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1.) At higher temperatures, these pyrazoline rings lose nitrogen to form cyclopropanes. The high yields of some of the thermal background reactions could be attributed to this process (Table 2, entries 1 and 2). The different yields of the thermal background reactions could be explained by the different boiling points of the solvents used under reflux conditions (Table 2).
    • (1948) J. Org. Chem. , vol.11 , pp. 67-74
    • Drake, N.L.1    Sweeney, T.R.2
  • 32
    • 0041775787 scopus 로고
    • Wiley: New York
    • EDA is known to thermally add to ethylenic linkages to form five-membered pyrazoline carboxylic esters via 1,3-dipolar cycloadditions. (See: Drake, N. L.; Sweeney, T. R. J. Org. Chem. 1948, 11, 67-74.1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1.) At higher temperatures, these pyrazoline rings lose nitrogen to form cyclopropanes. The high yields of some of the thermal background reactions could be attributed to this process (Table 2, entries 1 and 2). The different yields of the thermal background reactions could be explained by the different boiling points of the solvents used under reflux conditions (Table 2).
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.1
    • Padwa, A.1
  • 33
    • 0000926888 scopus 로고
    • It is known that styrene and EDA react at high temperatures to give the respective cyclopropane products when neat styrene is used (68% yield relative to EDA). See: Burger, A.; Yost, W. L. J. Am. Chem. Soc. 1948, 70, 2198-2201.
    • (1948) J. Am. Chem. Soc. , vol.70 , pp. 2198-2201
    • Burger, A.1    Yost, W.L.2
  • 34
    • 0000142576 scopus 로고
    • We note that Mukherjee and co-workers have observed that increasing the steric bulk at the 3- and 3′-positions causes the Fe-O-Fe moiety to be more linear but does not change the individual Fe-O bond length. See: Mukherjee, E. N.; Stack, T. D. P.; Holm, R. H. J. Am. Chem. Soc. 1988, 110, 1850-1861.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1850-1861
    • Mukherjee, E.N.1    Stack, T.D.P.2    Holm, R.H.3
  • 35
    • 0043279021 scopus 로고    scopus 로고
    • note
    • However, for catalyst 3d consistent, reproducible results could only be obtained under nitrogen.
  • 36
    • 0043279017 scopus 로고    scopus 로고
    • 2-Symmetric copper(ii) complexes as chiral lewis acids
    • Harvard University
    • 2-Symmetric Copper(II) Complexes as Chiral Lewis Acids, Postdoctoral Report, Harvard University, 1998.
    • (1998) Postdoctoral Report
    • Burgey, C.S.1    Evans, D.A.2
  • 45
    • 0043279016 scopus 로고
    • Ph.D. Thesis, Harvard University
    • Woerpel, K. A., Ph.D. Thesis, Harvard University, 1992.
    • (1992)
    • Woerpel, K.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.