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Volumn , Issue 18, 2010, Pages 3459-3464

Acid-catalysed or radical-promoted allylic substitution of 2-methylene-2, 3dihydrobenzofuran-3-ols with thiol derivatives: A novel and expedient synthesis of 2-(thiomethyl)benzofurans

Author keywords

Allylic substitution; Benzofurans; Nucleophilic substitution; Oxygen heterocycles; Radical reactions; Thioethers

Indexed keywords


EID: 77953273735     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000289     Document Type: Article
Times cited : (9)

References (69)
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    • For recent reviews on reactivity of thiols, see: a
    • For recent reviews on reactivity of thiols, see: a) I. V. Koval', Russ. J. Org. Chem. 2005, 41, 631-648;
    • (2005) Russ. J. Org. Chem. , vol.41 , pp. 631-648
    • Koval, I.V.1
  • 62
    • 34247359875 scopus 로고    scopus 로고
    • For a recent review on thiolmediated radical cyclization, see
    • b) I. V. Koval", Russ. J. Org. Chem. 2007, 43, 319-346. For a recent review on thiolmediated radical cyclization, see:
    • (2007) Russ. J. Org. Chem. , vol.43 , pp. 319-346
    • Koval, I.V.1
  • 64
    • 27644476270 scopus 로고    scopus 로고
    • A few examples of radical fragmentation to give rather highenergy radicals are known in the literature, but they involve the simultaneous formation of stabilized aromatic compounds; see, for example: a
    • A few examples of radical fragmentation to give rather highenergy radicals are known in the literature, but they involve the simultaneous formation of stabilized aromatic compounds; see, for example: a) J. C. Walton, A. Studer, Acc, Chem. Res. 2005, 38, 794-802;
    • (2005) Acc, Chem. Res. , vol.38 , pp. 794-802
    • Walton, J.C.1    Studer, A.2
  • 68
    • 0031048783 scopus 로고    scopus 로고
    • We are indebted to a referee for the suggestion of this mechanism. It is worth noting that radical cation formation under reductive conditions (also induced by an initial thiyl radical addition) for similar systems has been reported
    • We are indebted to a referee for the suggestion of this mechanism. It is worth noting that radical cation formation under reductive conditions (also induced by an initial thiyl radical addition) for similar systems has been reported: D. Crich, X.S. Mo, J. Am. Chem. Soc. 1997, 119, 249-250.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 249-250
    • Crich, D.1    Mo, X.S.2
  • 69
    • 33646949281 scopus 로고    scopus 로고
    • For a literature overview on ionic fragmentation of radical intermediates to give radical cations, see
    • For a literature overview on ionic fragmentation of radical intermediates to give radical cations, see: D. Crich, M. Shirai, F. Brebion, S. Rumthao, Tetrahedron 2006, 62, 6501-6518.
    • (2006) Tetrahedron , vol.62 , pp. 6501-6518
    • Crich, D.1    Shirai, M.2    Brebion, F.3    Rumthao, S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.