Palladium-Catalyzed Isomerization of Methylenecyclopropanes in Acetic Acid

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Abstract

Pd(PPh₃)₄-catalyzed isomerization of MCPs 1 in acetic acid proceeds smoothly at 80 °C in toluene to give the corresponding 1-substituted or 1,1-disubstituted dienes 2 in good to excellent yields under mild conditions. The plausible mechanism has been disclosed on the basis of a deuterium-labeling experiment.

Citing Articles

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This article has been cited by 11 ACS Journal articles (5 most recent appear below).

• 

  Chemistry of Vinylidenecyclopropanes

  Min Shi, Li-Xiong Shao, Jian-Mei Lu, Yin Wei, Kazuhiko Mizuno, and Hajime Maeda
  Chemical Reviews2010 110 (10), 5883-5913

  • Chemistry of Vinylidenecyclopropanes

    Min Shi, Li-Xiong Shao, Jian-Mei Lu, Yin Wei, Kazuhiko Mizuno, and Hajime Maeda
    Chemical Reviews2010 110 (10), 5883-5913
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Hydroformylation Reaction of Alkylidenecyclopropane Derivatives: A New Pathway for the Formation of Acyclic Aldehydes Containing Quaternary Stereogenic Carbons

  Samah Simaan and Ilan Marek
  Journal of the American Chemical Society2010 132 (12), 4066-4067

  • Hydroformylation Reaction of Alkylidenecyclopropane Derivatives: A New Pathway for the Formation of Acyclic Aldehydes Containing Quaternary Stereogenic Carbons

    Samah Simaan and Ilan Marek
    Journal of the American Chemical Society2010 132 (12), 4066-4067

    The rhodium-catalyzed hydroformylation reaction of methylene- and alkylidenecyclopropane derivatives proceeds under mild conditions to lead to the exclusive formation of linear aldehydes and the stereointegrity of the quaternary carbon center remains ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Lewis Acid Catalyzed Reaction of Methylenecyclopropanes with 1,2-Diphenyldiselane or 1,2-Di-p-tolyldisulfane

  Lei Yu, Jundong Meng, Ling Xia and Rong Guo
  The Journal of Organic Chemistry2009 74 (14), 5087-5089

  • Lewis Acid Catalyzed Reaction of Methylenecyclopropanes with 1,2-Diphenyldiselane or 1,2-Di-p-tolyldisulfane

    Lei Yu, Jundong Meng, Ling Xia and Rong Guo
    The Journal of Organic Chemistry2009 74 (14), 5087-5089

    Catalyzed by Lewis acid, 1,2-diphenyldiselane or 1,2-di-p-tolyldisulfane could add to methylenecyclopropanes smoothly. Compared with the reported free radical additions, the results were quite different. A four-membered carbon ring was constructed to ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Halohydroxylation of 1-Cyclopropylallenes: An Efficient and Stereoselective Method for the Preparation of Multisubstituted Olefins

  Lei Yu, Bo Meng and Xian Huang
  The Journal of Organic Chemistry2008 73 (17), 6895-6898

  • Halohydroxylation of 1-Cyclopropylallenes: An Efficient and Stereoselective Method for the Preparation of Multisubstituted Olefins

    Lei Yu, Bo Meng and Xian Huang
    The Journal of Organic Chemistry2008 73 (17), 6895-6898
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Substrate-Controlled Selective Proximal and Distal C−C Bond Cleavage via Lewis Acid Mediated O-Acylation of 2-(Arylmethylene)cyclopropylaldehyde: A Stereoselective Synthesis of Bifunctional Methylenecyclobutanes and 1,3-Conjugated Dienes

  Xian Huang and Maozhong Miao
  The Journal of Organic Chemistry2008 73 (17), 6884-6887

  • Substrate-Controlled Selective Proximal and Distal C−C Bond Cleavage via Lewis Acid Mediated O-Acylation of 2-(Arylmethylene)cyclopropylaldehyde: A Stereoselective Synthesis of Bifunctional Methylenecyclobutanes and 1,3-Conjugated Dienes

    Xian Huang and Maozhong Miao
    The Journal of Organic Chemistry2008 73 (17), 6884-6887

    ZnCl2-mediated reactions of (E)-2-(arylmethylene)cyclopropylaldehyde 1 with various acyl chlorides provide a novel method for stereoselective synthesis of bifunctional methlylenecyclobutanes via a proximal-bond cleavage process. Nevertheless, when (Z)-1 ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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