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Volumn 15, Issue 46, 1974, Pages 4029-4032

Facile syntheses of 12-crown-4 and 15-crown-5

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[No Author keywords available]

Indexed keywords


EID: 0008391350     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)92075-1     Document Type: Article
Times cited : (65)

References (44)
  • 4
    • 84918275676 scopus 로고    scopus 로고
    • For reviews on crown ether chemistry, see:
  • 13
    • 84918275675 scopus 로고    scopus 로고
    • 1,4,7,10,13,16-Hexaoxacyclooctadecane;
  • 15
    • 84918275674 scopus 로고    scopus 로고
    • G.W. Gokel, D.J. Cram, R.P. Harris, C.L. Liotta, and F.L. Cook, Organic Syntheses submitted for publication.
  • 16
    • 84918275673 scopus 로고
    • Abstract
    • Mass.
    • C.L. Liotta, and H.P. Harris, First Fall Organic Conference, Cape Cod, Mass., Oct. 1, 1973, Abstract No. 5
    • (1973) Abstract , Issue.5
    • Liotta1    Harris2    Fall3    Conference4    Cod5
  • 20
    • 84918275670 scopus 로고    scopus 로고
    • F.L. Cook, H.P. Harris, T.R. Henson, W.C. Tincher, and C.L. Liotta J. Org. Chem., submitted for publication.
  • 24
    • 84918275669 scopus 로고    scopus 로고
    • Professor R. A. Bartsch, private communication.
  • 28
    • 84918275668 scopus 로고    scopus 로고
    • D.G. Stewart, D.Y. Waddan, and E.T. Borrows Brit. Pat. 785, 229 (1957)
  • 31
    • 84918275667 scopus 로고    scopus 로고
    • J. Dale, G. Borgen, and K. Daasvatn, Norw. Pat. Application (1973)
  • 36
    • 84918275665 scopus 로고    scopus 로고
    • 4, in THF instead of in DMSO.
  • 37
    • 84918275664 scopus 로고    scopus 로고
    • Other systems using THF or DMSO as solvents for using KOH instead of NaOH proved to be less satisfactory.
  • 40
    • 84918275662 scopus 로고    scopus 로고
    • Raising the temperature of the glycol-base solution to 110°C before addition of the chloride did not affect the yield.
  • 41
    • 84918275661 scopus 로고    scopus 로고
    • A trace of DMSO in the final product was eliminated by redistillation.
  • 42
    • 84918275660 scopus 로고    scopus 로고
    • Infrared analysis showed water to be present in the isolated product, probably in the form of the hydrate. The water was removed by allowing the crown to stir over molecular sieve adsorbent under nitrogen for ca. 12 hours.
  • 43
    • 84918275659 scopus 로고    scopus 로고
    • NMR analysis showed that a fraction collected from 90–100°C at 0.2 mm Hg also contained some crown, but consisted mainly of triethylene glycol.
  • 44
    • 84918275658 scopus 로고    scopus 로고
    • Slow, careful redistillation of the product gave a constant boiling point of 78°C at 0.05 mm Hg.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.