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Volumn 128, Issue 50, 2006, Pages 16358-16364

p-tert-butylcalix[4]arene complexes of molybdenum and tungsten: Reactivity of the calixarene methylene C-H bond and the facile migration of the metal around the phenolic rim of the calixarene

Author keywords

[No Author keywords available]

Indexed keywords

DEUTERIUM; HYDRIDES; ISOMERS; MOLYBDENUM COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TUNGSTEN;

EID: 33845591352     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066457b     Document Type: Article
Times cited : (41)

References (90)
  • 1
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    • (a) Gutsche, C. D. Calixarenes: Royal Society of Chemistry: Cambridge, 1989.
    • (1989) Calixarenes
    • Gutsche, C.D.1
  • 15
  • 26
    • 0007507712 scopus 로고    scopus 로고
    • See for example
    • In addition, high valent molybdenum and tungsten complexes of the larger p-tert-butylcalix[5]arene, p-tert-butylcalix[6]arene, and p-tert-butylcalix[8] arene derivatives have also been synthesized. See for example: (a) Fan, M.; Zhang, H.; Lattman, M. Chem. Commun. 1998, 99-100.
    • (1998) Chem. Commun. , pp. 99-100
    • Fan, M.1    Zhang, H.2    Lattman, M.3
  • 35
    • 0002087304 scopus 로고
    • and 31-37
    • 3) distance for compounds listed in the Cambridge Structural Database is 2.23 Å. CSD Version 5.27. 3D Search and Research Using the Cambridge Structural Database; Allen, F. H.; Kennard, O. Chemical Design Automation News 1993, 8 (1), pp 1 and 31-37.
    • (1993) Chemical Design Automation News , vol.8 , Issue.1 , pp. 1
    • Allen, F.H.1    Kennard, O.2
  • 36
    • 33845593200 scopus 로고    scopus 로고
    • note
    • 2] is intended to indicate that a hydrogen atom has been removed from one of the methylene groups.
  • 39
    • 33845590415 scopus 로고    scopus 로고
    • note
    • For other examples which show that tungsten has a greater ability to achieve C-H bond cleavage than does molybdenum, see ref 6.
  • 40
    • 33845577813 scopus 로고    scopus 로고
    • note
    • 4] yields a compound in which two calixarene units become linked via an ether function resulting from the coupling of a phenol group with a methylene group (ref 3m). While this transformation formally involves cleavage of a methylene C-H group, an alkyl hydride complex was not observed.
  • 48
    • 0000173807 scopus 로고    scopus 로고
    • see
    • For other examples where a metal serves the role as a hydrogen bond acceptor, see: (a) Martin, A. J. Chem. Educ. 1999, 76, 578-583.
    • (1999) J. Chem. Educ. , vol.76 , pp. 578-583
    • Martin, A.1
  • 58
    • 33845581504 scopus 로고    scopus 로고
    • note
    • 8 M⋯H-C species, see ref 13c.
  • 61
    • 33845569993 scopus 로고    scopus 로고
    • note
    • 2 has also been reported to adopt a partial cone conformation. See ref 16.
  • 62
    • 33845583375 scopus 로고    scopus 로고
    • note
    • -1).
  • 63
    • 33845567972 scopus 로고    scopus 로고
    • note
    • -1) for molybdenum.
  • 67
    • 33845570329 scopus 로고    scopus 로고
    • note
    • 2 is 99 Hz.
  • 69
    • 33845574626 scopus 로고    scopus 로고
    • note
    • Evidence for migration has also been noted for a dinuclear rhodium calixarene derivative (ref 12c). Furthermore, an irreversible migration has been inferred from the formation of a 1.2-platinum compound from a 1,3-bis(trimethylsilyl)calixarene ether (ref 12a).
  • 70
    • 0000873890 scopus 로고
    • See
    • Notably, there is no exchange between endo and exo hydrogen atoms of each methylene group indicating that the cone-cone interconversion observed for the free calixarene does not occur on a similar time scale. See: Gutsche, C. D.; Bauer, L. J. J. Am. Chem. Soc. 1985, 107, 6052-6059.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 6052-6059
    • Gutsche, C.D.1    Bauer, L.J.2
  • 71
    • 33845574433 scopus 로고    scopus 로고
    • note
    • H) also exchanges sites with the endo hydrogen atoms. However, this process was not detected by the EXSY experiment because the agostic hydrogen preferentially exchanges with the hydride sites.
  • 73
    • 0002820924 scopus 로고
    • Wayda, A. L., Darensbourg, M. Y., Eds.; American Chemical Society: Washington, DC; Chapter 2
    • (a) McNally, J. P.; Leong, V. S.; Cooper, N. J. In Experimental Organometallic Chemistry; Wayda, A. L., Darensbourg, M. Y., Eds.; American Chemical Society: Washington, DC, 1987; Chapter 2, pp 6-23.
    • (1987) Experimental Organometallic Chemistry , pp. 6-23
    • McNally, J.P.1    Leong, V.S.2    Cooper, N.J.3
  • 74
    • 0002522541 scopus 로고
    • Wayda, A. L., Darensbourg, M. Y., Eds.; American Chemical Society: Washington, DC; Chapter 4
    • (b) Burger, B. J.; Bercaw, J. E. In Experimental Organometallic Chemistry; Wayda, A. L., Darensbourg, M. Y., Eds.; American Chemical Society: Washington, DC, 1987; Chapter 4, pp 79-98.
    • (1987) Experimental Organometallic Chemistry , pp. 79-98
    • Burger, B.J.1    Bercaw, J.E.2
  • 77
    • 33845586310 scopus 로고    scopus 로고
    • "CIL NMR Solvent Data Chart", Cambridge Isotope Laboratories, Inc., Andover, MA 01810-5413, U.S.A.
    • "CIL NMR Solvent Data Chart", Cambridge Isotope Laboratories, Inc., Andover, MA 01810-5413, U.S.A.
  • 82
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    • Jaguar 6.5; Schrödinger, LLC: New York, NY, 2005.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.