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Volumn 68, Issue 21, 2003, Pages 8248-8251

Zn(II)-catalyzed thiolysis of oxiranes in water under neutral conditions

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Indexed keywords

CATALYST RECOVERY;

EID: 0142058449     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0348266     Document Type: Article
Times cited : (111)

References (56)
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    • 0142088369 scopus 로고    scopus 로고
    • note
    • The epoxidation of homo- and bis-homoallylic alcohols and the ring-opening of the corresponding oxiranes in organic medium is often accompanied by the formation of hydroxy tetrahydrofuran and tetrahydropyran derivatives.17 In our case, the preparation of 1,2-epoxide 9 has been performed in water at pH 7.0 by oxidation of the corresponding alkene (10 mmol) with m-chloroperbenzoic acid (m-CPBA, 30 mmol), and the pH has been kept constant for the entire reaction time (2 h). With this procedure, we did not find any tetrahydrofuran or tetrahydropyrans derivatives as byproducts and the 5,6-epoxy-1-hexanol (9) has been obtained in 85% yield after workup of the reaction mixture.
  • 56
    • 0142088370 scopus 로고    scopus 로고
    • note
    • In the first run, 1.5 equiv of thiophenol was used according to the standard procedure (see the Experimental Section). In the subsequent runs, 1.0 equiv of thiol was used and the reaction conversion was 100%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.