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. 2003 Jan 3;42(1):98-101.
doi: 10.1002/anie.200390064.

1,2-Migration of the thio group in allenyl sulfides: efficient synthesis of 3-thio-substituted furans and pyrroles

Joseph T Kim  1 , Alexander V Kel'in, Vladimir Gevorgyan
Affiliations

1,2-Migration of the thio group in allenyl sulfides: efficient synthesis of 3-thio-substituted furans and pyrroles

Joseph T Kim et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Scheme 1
Scheme 1
Different routes for the cyclization of the ketopropargyl sulfide 1 to give either furan 2 or 3. Based on this mechanistic proposal, the reaction of ketopropargyl sulfides in which Hb of 4 is replaced with any other nonmigrating group should exclusively follow path b.
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References

    1. Johnston BD, Pinto BM. J. Org. Chem. 2000;65:4607. - PubMed
    2. Yu B, Yang Z. Org. Lett. 2001;3:377. - PubMed
    3. Viso A, Poopeiko N, Castillon S. Tetrahedron Lett. 2000;41:407.
    1. Plate R, Nivard RJF, Ottenheijm HCJ. Tetrahedron. 1986;42:4503.
    2. Hamel P. J. Org. Chem. 2002;67:2854. - PubMed
    3. Volontereo A, Zanda M, Bravo P, Fronza G, Cavicchio G, Crucianelli M. J. Org. Chem. 1997;62:8031. - PubMed
    1. Kel'in AV, Gevorgyan V. J. Org. Chem. 2002;67:95. - PubMed
    1. Kelcin AV, Sromek AW, Gevorgyan V. J. Am. Chem. Soc. 2001;123:2074. - PubMed

    1. For an example of propargyl–allenyl isomerization, see: Garratt PJ, Neoh SB. J. Am. Chem. Soc. 1975;97:3255.

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