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Volumn 32, Issue 23, 1991, Pages 2675-2678

syn-1,2-dialkylated calix[4]arenes : general intermediates in the NaH/DMF tetraalkylation of calix[4]arenes

Author keywords

Calix 4 arenes; Cation Effect; Intermediate Anions; Solvent Effect; Tetraalkylation

Indexed keywords

MACROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON;

EID: 0025732504     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)78816-2     Document Type: Article
Times cited : (131)

References (18)
  • 1
    • 0004146786 scopus 로고
    • F.J. Stoddart, The Royal Society of Chemistry, Cambridge, Monographs in Supramolecular Chemistry
    • (1989) Calixarenes , vol.1
    • Gutsche1
  • 9
    • 0024834438 scopus 로고
    • The first and till now only syn-1,2-disubstituted calix[4]arenes that were synthesized by direct substitution are the bis[(2-pyridyl)methyl] ethers of 1a and 1b.
    • (1989) J. Org. Chem. , vol.54 , pp. 5407-5409
    • Bottino1    Giunta2    Pappalardo3
  • 10
    • 84918615891 scopus 로고    scopus 로고
    • 9
  • 12
    • 84918653254 scopus 로고    scopus 로고
    • The new compounds 2–5 and the cone conformer of the tetraethyl ether of 1b showed satisfactory spectroscopic and elemental analyses.
  • 13
    • 84918606338 scopus 로고    scopus 로고
    • 1H NMR spectrum of the crude reaction mixture was recorded in order to determine its composition. Unreacted calix[4]arene and the mono, syn-1,2-di, and syn-1,3-dialkylated intermediates were distinguished by their characteristic OH signals at δ 10.4-10.2, 10.2-9.8 and 9.6-9.2 (1 : 2), 9.1-8.6, and 7.9-7.5, respectively. Tetrasubstituted products (cone) could in some cases be detected.
  • 14
    • 84918627925 scopus 로고    scopus 로고
    • 13,14 we observed that, after heating a solution of the cone in DMF with NaH at 50 °C for 24 h, the cone had partly isomerized to the partial cone conformer, the ratio of cone to partial cone being 1 : 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.