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Tetrahedron Letters
Volumn 19, Issue 33, 1978, Pages 2991-2994
A convenient route to cyclopropanone dithioketals. The thiophenoxide anion as a nucleofugal leaving group
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EID: 0002279656     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)94920-2     Document Type: Article
Times cited : (24)
References (21)
  • 1
    • 84982061441 scopus 로고
    • Darstellung und “disproportionierende Hydrolyse” von Cyclopropanonthioacetalen Eine neue Homologisierungsmethode1, 2)
    • Two of the best methods are described in a paper which also reviews all other known methods
    • (1976) Chemische Berichte , vol.109 , pp. 669
    • Braun1    Seebach2
  • 2
    • 84917996398 scopus 로고    scopus 로고
    • 1H NMR, infrared, and mass spectroscopy. Elemental compositions were determined for all new compounds either by combustion analysis or exact mass determination.
  • 4
    • 0000948995 scopus 로고
    • The first observation of such ring closures was made by Dr. D. W. Shull when this thioacetal was treated with methyllithium in order to exchange the thioacetal proton for a deuteron. The preparation of both labeled and unlabeled thioacetals is described in:
    • (1976) J. Org. Chem. , vol.41 , pp. 3218
    • Cohen1    Mura2    Shull3    Fogel4    Ruffner5    Falck6
  • 5
    • 0343248257 scopus 로고
    • These compounds are prepared in over 90% yield from commercially available allyl or methallyl phenyl sulfide
    • (1976) J. Org. Chem. , vol.41 , pp. 2506
    • Cohen1    Bennett2    Mura3
  • 6
    • 84917996397 scopus 로고    scopus 로고
    • Aldrich Chemical Company.
  • 7
    • 33847088706 scopus 로고
    • For a review of the capture of carbenes by thioethers and Stevens rearrangement of the resulting ylides, see
    • (1977) Acc. Chem. Res. , vol.10 , pp. 179
    • Ando1
  • 8
    • 84982446988 scopus 로고
    • Tris-phenylmercapto-methyllithium Ein ungewöhnliches Carbenoid
    • and references there cited
    • (1972) Chemische Berichte , vol.105 , pp. 487
    • Seebach1
  • 10
    • 84917996396 scopus 로고    scopus 로고
    • T. Cohen and W. M. Daniewski, unpublished observations
  • 13
    • 84943901253 scopus 로고
    • INTRAMOLECULAR FORMATION OF YLIDES FROM CARBENES BEARING SULFUR ATOM ON γ-POSITION
    • (1972) Chemistry Letters , pp. 119
    • Kondo1    Ojima2
  • 14
    • 84917996394 scopus 로고    scopus 로고
    • 1,1,4-Tris(phenylthio)butane was prepared in 60% yield by treatment of 1-bromo-3(phenylthio)propane (from the reaction of sodium thiophenoxide with a 10 fold excess of 1,3-dibromopropane in ethanol; 92% yield) with bis(phenylthio)methyllithium in THF containing TMEDA (0°→25°). 1,1,5-Tris(phenylthio)pentane was prepared by an analogous sequence starting from 1,4-dibromobutane.
  • 17
    • 0000646035 scopus 로고
    • Trost has elegantly exploited the parent of this class in a variety of synthetic techniques which at present are limited by the unavailability of substituted derivatives.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 3088
    • Trost1    Keeley2    Arndt3    Bogdanowicz4
  • 18
    • 0344716655 scopus 로고
    • The recent use of cyclopropyllithium compounds and the derived cuprates in the preparation of vinylcyclopropanes suggest other interesting uses of these anions.
    • (1976) J. Org. Chem. , vol.41 , pp. 3629
    • Marino1    Browne2

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.