Literature DB >> 17107075

Synthesis of novel pentafluorosulfanylfurans. Two retro-Diels-Alder approaches.

William R Dolbier1, Akira Mitani, Wei Xu, Ion Ghiviriga.   

Abstract

The first examples of furan substituted with an SF5 group are reported. 3-pentafluorosulfanylfurans were prepared from their respective 2-pentafluorosulfanyl-5-cyano-7-oxabicyclo[2.2.1]hept-2-ene precursors via retro-Diels-Alder reactions. Also, a tandem cycloaddition/retrocycloaddition reaction between 4-phenyloxazole and 1-pentafluorosulfanylhex-1-yne was used to prepare 3-pentafluorosulfanyl-4-butylfuran. [reaction: see text].

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Year:  2006        PMID: 17107075     DOI: 10.1021/ol0622662

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.

Authors:  Yvonne D Williams; Christine Meck; Noushad Mohd; Ryan P Murelli
Journal:  J Org Chem       Date:  2013-11-14       Impact factor: 4.354

2.  Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of "super-trifluoromethyl" arene chemistry and its industry.

Authors:  Teruo Umemoto; Lloyd M Garrick; Norimichi Saito
Journal:  Beilstein J Org Chem       Date:  2012-03-29       Impact factor: 2.883

3.  Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes.

Authors:  Anna-Lena Dreier; Andrej V Matsnev; Joseph S Thrasher; Günter Haufe
Journal:  Beilstein J Org Chem       Date:  2018-02-08       Impact factor: 2.883

  3 in total

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