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Volumn , Issue 22, 2000, Pages 3721-3725

α-Oxosulfines, IV: Intramolecular hetero diels-alder reactions of α,α′-dioxosulfines - A new access to the [3.3.1]-bicyclic skeleton

Author keywords

Cycloadditions; Dioxosulfines; Intramolecular reactions; Retro reactions; Sulfur heterocycles

Indexed keywords

ALKADIENE; ALPHA,ALPHA' DIOXOTHIONE DERIVATIVE; CARBONYL DERIVATIVE; OXATHIIN DERIVATIVE; OXIDE; POLYCYCLIC HYDROCARBON; THIOKETONE; UNCLASSIFIED DRUG;

EID: 0033710133     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200011)2000:22<3721::AID-EJOC3721>3.0.CO;2-B     Document Type: Article
Times cited : (6)

References (26)
  • 14
    • 37049103756 scopus 로고
    • The reaction of phthalimidesulfenyl chloride with alkenes is a quantitative process leading to precursors of episulfides: M. U. Bombala, S. V. Ley, J. Chem. Soc., Perkin Trans. 1 1979, 3013-3016.
    • (1979) J. Chem. Soc., Perkin Trans. 1 , pp. 3013-3016
    • Bombala, M.U.1    Ley, S.V.2
  • 15
    • 19444372124 scopus 로고    scopus 로고
    • note
    • All attempts to obtain the acid 3b from the corresponding ethyl ester were unfruitful, whether under acidic or basic conditions.
  • 16
    • 19444387821 scopus 로고    scopus 로고
    • note
    • As a further demonstration of the effectiveness of oxidation at sulfur in controlling the retro Diels-Alder processes, sulfides 3a and 7a and 7b are perfectly stable in refluxing THF.
  • 19
    • 19444377568 scopus 로고    scopus 로고
    • note
    • The rate of formation of compound 12a from 10b can be increased by heating 9a in benzene at 80 °C (72 h vs. 240 h): however, under these conditions, the yield of 12a is lower (15%) and some quantities of the corresponding β-keto ester (allyl-3-oxobutanoate) can be isolated.
  • 20
    • 19444387152 scopus 로고    scopus 로고
    • note
    • Also in this case, using a mixture of cis and trans sulfoxides, we can appreciate the quite fast reaction of cis isomer to give the final product and/or the trans sulfoxide.
  • 21
    • 19444373524 scopus 로고    scopus 로고
    • AM1 Molecular mechanics semi-empirical calculation
    • AM1 Molecular mechanics semi-empirical calculation.
  • 26
    • 19444374560 scopus 로고    scopus 로고
    • note
    • Unfortunately, the quality of crystals of compounds 12a and 12b does not allow an X-ray analysis. Moreover, probably because of a retro Diels-Alders process and/or loss of sulfur monoxide, derivatives 12 underwent decomposition on heating without any defined melting point.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.