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Volumn 70, Issue 24, 2005, Pages 10198-10201

A high-yield, one-step synthesis of o-phenylene ethynylene cyclic trimer via precipitation-driven alkyne metathesis

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; PRECIPITATION (CHEMICAL); THERMODYNAMICS;

EID: 28144463382     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0517803     Document Type: Article
Times cited : (69)

References (39)
  • 8
    • 0001854116 scopus 로고
    • Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, Chapter 12
    • (h) Young, J. K.; Moore, J. S. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 12.
    • (1995) Modern Acetylene Chemistry
    • Young, J.K.1    Moore, J.S.2
  • 15
    • 0001083913 scopus 로고    scopus 로고
    • and ref 1f
    • (c) Haley, M. M. Synlett 1998, 557-565 and ref 1f.
    • (1998) Synlett , pp. 557-565
    • Haley, M.M.1
  • 24
    • 5644250509 scopus 로고    scopus 로고
    • Zhang, W.; Moore, J. S. J. Am. Chem. Soc. 2004, 126, 12796. Bunz previously reported the synthesis of hexameric macrocycles via alkyne metathesis. Under their conditions, which required high temperature (150 °C), the desired products were obtained in only 0.5-6% yields.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12796
    • Zhang, W.1    Moore, J.S.2
  • 33
    • 28144436707 scopus 로고    scopus 로고
    • note
    • See the Experimental Section for detailed characterization data.
  • 34
    • 28144460051 scopus 로고    scopus 로고
    • note
    • Macrocycle 6 was synthesized from the corresponding m-dialkoxybenzene monomer via precipitation-driven alkyne metathesis (see the Supporting Information for details). On MALDI-MS of the metathesis product, only hexameric (m/z = 1800) and pentameric (m/z = 1500) macrocycles were observed. Such a macrocycle mixture was subjected to the subsequent scrambling metathesis experiment without further separation.
  • 35
    • 0038813200 scopus 로고    scopus 로고
    • Höger applied a template-cyclization to synthesize phenylene ethynylene macrocycles in excellent yields. However, the covalently attached templates require the introduction of specific functional groups into the cyclization precursors, and extra synthetic steps are needed for attachment and cleavage. See; (a) Höger, S. J. Polym. Sci. Part A: Polym. Chem. 1999, 37, 2685-2698.
    • (1999) J. Polym. Sci. Part A: Polym. Chem. , vol.37 , pp. 2685-2698
    • Höger, S.1
  • 38
    • 33746343775 scopus 로고
    • Sanders utilized noncovalent template approach in synthesis of large shape-persistent rings. Cyclic porphyrin oligomers were obtained in 50-70% yield, (a) Anderson, H. L.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1400-1403.
    • (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 1400-1403
    • Anderson, H.L.1    Sanders, J.K.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.