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Volumn 81, Issue 5, 2013, Pages 399-401

Multiple alkylation of thiophene derivatives with simple and extended diarylcarbenium ion pools

Author keywords

Alkylation; Diarylcarbenium ion; Electrochemical oxidation; Thiophene

Indexed keywords

ALKYLATION PRODUCTS; BITHIOPHENES; DENDRITIC MOLECULE; TERTHIOPHENES; THIOPHENE DERIVATIVES;

EID: 84878994427     PISSN: 13443542     EISSN: 21862451     Source Type: Journal    
DOI: 10.5796/electrochemistry.81.399     Document Type: Article
Times cited : (10)

References (32)
  • 4
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    • A review on Friedel-Crafts reactions:, Pergamon Press, Oxford
    • A review on Friedel-Crafts reactions: H. Heaney, Comprehensive Organic Synthesis, Vol. 2, Pergamon Press, Oxford, p. 733 (1991).
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 733
    • Heaney, H.1
  • 24
    • 64649106986 scopus 로고    scopus 로고
    • Recent review of functional oligothiophenes
    • Recent review of functional oligothiophenes: A. Mishra, C.-Q. Ma, and P. Bäuerle, Chem. Rev., 109, 1141 (2009).
    • (2009) Chem. Rev. , vol.109 , pp. 1141
    • Mishra, A.1    Ma, C.-Q.2    Bäuerle, P.3
  • 29
    • 84878973137 scopus 로고    scopus 로고
    • The anodic oxidation was carried out in 0.3M Bu4NBF4/CH2Cl2 (8.0mL for both chamber) using a divided cell equipped with a carbon felt anode and a platinum plate cathode. In the anodic and cathodic chamber 4, 4B-difluorodiphenylmethane (1) (0.92 mmol) and TfOH (70 μL) were placed, respectively, and the constant current electrolysis (20 mA, 2.5 F/mol-1) was carried out at 178°C. After the electrolysis, thiophene (0.17 mmol) was added to the anodic chamber and the reaction mixture was stirred for another 90 min. Then Et3N was added and the reaction mixture was filtered through a short column of silica gel (d: 2 cm, h: 3 cm). After removal of solvent, the crude product was purified with preparative GPC to obtain 3a and 3b in 58% (56 mg, 0.096 mmol) and 24% (17 mg, 0.040 mmol) yields, respectively
    • The anodic oxidation was carried out in 0.3M Bu4NBF4/CH2Cl2 (8.0mL for both chamber) using a divided cell equipped with a carbon felt anode and a platinum plate cathode. In the anodic and cathodic chamber 4, 4B-difluorodiphenylmethane (1) (0.92 mmol) and TfOH (70 μL) were placed, respectively, and the constant current electrolysis (20 mA, 2.5 F/mol-1) was carried out at 178°C. After the electrolysis, thiophene (0.17 mmol) was added to the anodic chamber and the reaction mixture was stirred for another 90 min. Then Et3N was added and the reaction mixture was filtered through a short column of silica gel (d: 2 cm, h: 3 cm). After removal of solvent, the crude product was purified with preparative GPC to obtain 3a and 3b in 58% (56 mg, 0.096 mmol) and 24% (17 mg, 0.040 mmol) yields, respectively.
  • 30
    • 84878997892 scopus 로고    scopus 로고
    • CCDC 745439 contains crystallographic data for 4a
    • CCDC 745439 contains crystallographic data for 4a.
  • 32
    • 84878974013 scopus 로고    scopus 로고
    • Tetra-, penta-, and hexa-alkylated products of 1, 3, 5-tris(2B-thienyl) benzene were observed by mass-spectroscopy. These products were not separable probably because of the low regioselectivity of alkylation towards 1, 3, 5-tris(2B-thienyl)- benzene
    • Tetra-, penta-, and hexa-alkylated products of 1, 3, 5-tris(2B-thienyl) benzene were observed by mass-spectroscopy. These products were not separable probably because of the low regioselectivity of alkylation towards 1, 3, 5-tris(2B-thienyl)- benzene.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.