Intramolecular [4+2] Cycloaddition Reactions of Conjugated Enynes

Rick L. Danheiser, Alexandra E. Gould, Roberto Fernandez de la Pradilla, Anna L. Helgason
J. Org. Chem., 1994, 59 (19), pp 5514–5515
DOI: 10.1021/jo00098a002
Publication Date: September 1994
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This article has been cited by 38 ACS Journal articles (5 most recent appear below).

  • Cover Image

    Concerted vs Stepwise Mechanisms in Dehydro-Diels–Alder Reactions

    Aida Ajaz, Alexander Z. Bradley, Richard C. Burrell, William Hoi Hong Li, Kimberly J. Daoust, Laura Boddington Bovee, Kenneth J. DiRico, and Richard P. Johnson
    The Journal of Organic Chemistry2011 76 (22), 9320-9328
    • Concerted vs Stepwise Mechanisms in Dehydro-Diels–Alder Reactions

      Aida Ajaz, Alexander Z. Bradley, Richard C. Burrell, William Hoi Hong Li, Kimberly J. Daoust, Laura Boddington Bovee, Kenneth J. DiRico, and Richard P. Johnson
      The Journal of Organic Chemistry2011 76 (22), 9320-9328

      The Diels–Alder reaction is not limited to 1,3-dienes. Many cycloadditions of enynes and a smaller number of examples with 1,3-diynes have been reported. These “dehydro”-Diels–Alder cycloadditions are one class of dehydropericyclic reactions which have ...

  • Cover Image

    Mild and Tunable Benzoic Acid Catalysts for Rearrangement Reactions of Allylic Alcohols

    J. Adam McCubbin, Samantha Voth, and Oleg V. Krokhin
    The Journal of Organic Chemistry2011 76 (20), 8537-8542
    • Mild and Tunable Benzoic Acid Catalysts for Rearrangement Reactions of Allylic Alcohols

      J. Adam McCubbin, Samantha Voth, and Oleg V. Krokhin
      The Journal of Organic Chemistry2011 76 (20), 8537-8542

      An efficient and simple catalytic method for the isomerization of readily prepared allylic alcohols is described. We focus particularly on cyclic examples and the synthesis of unusual enyne and dienols. The benzoic acid catalysts employed are commercially ...

  • Cover Image

    Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones

    Thomas G. Back, Kristen N. Clary and Detian Gao
    Chemical Reviews2010 110 (8), 4498-4553
    • Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones

      Thomas G. Back, Kristen N. Clary and Detian Gao
      Chemical Reviews2010 110 (8), 4498-4553
  • Cover Image

    Enyne [4 + 4] Photocycloaddition: Bridged 1,2,5-Cyclooctatrienes

    Svitlana Kulyk, William G. Dougherty, Jr., W. Scott Kassel, Steven A. Fleming and Scott McN. Sieburth
    Organic Letters2010 12 (15), 3296-3299
    • Enyne [4 + 4] Photocycloaddition: Bridged 1,2,5-Cyclooctatrienes

      Svitlana Kulyk, William G. Dougherty, Jr., W. Scott Kassel, Steven A. Fleming and Scott McN. Sieburth
      Organic Letters2010 12 (15), 3296-3299

      Enyne photocycloaddition with a 2-pyridone yields a mixture of products including amide-bridged 1,2,5-cyclooctatrienes, the first examples of enyne [4 + 4] adducts. Four regio- and stereochemical isomers of the [4 + 4] adduct are possible. All appear to ...

  • Cover Image

    The Dehydro-Diels−Alder Reaction

    Pablo Wessig and Gunnar Müller
    Chemical Reviews2008 108 (6), 2051-2063

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