Epoxidation of Alpha-Methylstyrene and its Lewis Acid Rearrangement to 2-Phenylpropanal

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Abstract

Citing Articles

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This article has been cited by 7 ACS Journal articles (5 most recent appear below).

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  The Discovery-Oriented Approach to Organic Chemistry. 7. Rearrangement of trans-Stilbene Oxide with Bismuth Trifluoromethanesulfonate and Other Metal Triflates. A Microscale Green Organic Chemistry Laboratory Experiment

  James E. Christensen , Matthew G. Huddle , Jamie L. Rogers , Herbie Yung and Ram S. Mohan
  Journal of Chemical Education2008 85 (9), 1274

  • The Discovery-Oriented Approach to Organic Chemistry. 7. Rearrangement of trans-Stilbene Oxide with Bismuth Trifluoromethanesulfonate and Other Metal Triflates. A Microscale Green Organic Chemistry Laboratory Experiment

    James E. Christensen , Matthew G. Huddle , Jamie L. Rogers , Herbie Yung and Ram S. Mohan
    Journal of Chemical Education2008 85 (9), 1274

    Although green chemistry principles are increasingly stressed in the undergraduate curriculum, there are only a few lab experiments wherein the toxicity of reagents is taken into consideration in the design of the experiment. We report a microscale green ...

    Abstract | Hi-Res PDF | PDF w/ Links
• 

  A Series of Small-Scale, Discovery-Based Organic Laboratory Experiments Illustrating the Concepts of Addition, Substitution, and Rearrangement

  Judith S. Moroz , Janice L. Pellino and Kurt W. Field
  Journal of Chemical Education2003 80 (11), 1319

  • A Series of Small-Scale, Discovery-Based Organic Laboratory Experiments Illustrating the Concepts of Addition, Substitution, and Rearrangement

    Judith S. Moroz , Janice L. Pellino and Kurt W. Field
    Journal of Chemical Education2003 80 (11), 1319

    Multistep, microscale organic laboratory experiments are presented that illustrate addition, substitution, and rearrangement reactions. The sequence begins with the preparation of 1,2-dichloro-1,1,2,2-tetraphenylethane, 2, from tetraphenylethene, 1, and ...

    Abstract | Hi-Res PDF | PDF w/ Links
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  Diastereoselective Synthesis of a Strawberry Flavoring Agent by Epoxidation of Ethyl trand-beta-Methylcinnamate

  Gayle J. Pageau , Rodwell Mabaera , Kathryn M. Kosuda , Tamara A. Sebelius , Ali H. Ghaffari , Kenneth A. Kearns , Jean P. McIntyre , Tina M. Beachy and Dasan M. Thamattoor
  Journal of Chemical Education2002 79 (1), 96

  • Diastereoselective Synthesis of a Strawberry Flavoring Agent by Epoxidation of Ethyl trand-beta-Methylcinnamate

    Gayle J. Pageau , Rodwell Mabaera , Kathryn M. Kosuda , Tamara A. Sebelius , Ali H. Ghaffari , Kenneth A. Kearns , Jean P. McIntyre , Tina M. Beachy and Dasan M. Thamattoor
    Journal of Chemical Education2002 79 (1), 96

    The diastereoselective synthesis of ethyl (E)-3-methyl-3-phenylglycidate, a strawberry flavoring agent, is carried out by epoxidizing ethyl trans-β-methylcinnamate with m-chloroperbenzoic acid. This epoxidation is appropriate for the introductory organic ...

    Abstract | Hi-Res PDF | PDF w/ Links
• 

  Synthesis and Use of Jacobsen's Catalyst: Enantioselective Epoxidation in the Introductory Organic Laboratory

  John Hanson
  Journal of Chemical Education2001 78 (9), 1266

  • Synthesis and Use of Jacobsen's Catalyst: Enantioselective Epoxidation in the Introductory Organic Laboratory

    John Hanson
    Journal of Chemical Education2001 78 (9), 1266

    Jacobsen's catalyst, N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride, is a popular reagent for the enantioselective epoxidation of alkenes. This reagent is successfully prepared in three steps by beginning organic ...

    Abstract | Hi-Res PDF | PDF w/ Links
• 

  The Discovery-Oriented Approach to Organic Chemistry. 4. Epoxidation of p-Methoxy-trans-β[beta]-methylstyrene: An Exercise in NMR and IR Spectroscopy for Sophomore Organic Laboratories

  Rebecca S. Centko and Ram S. Mohan
  Journal of Chemical Education2001 78 (1), 77

  • The Discovery-Oriented Approach to Organic Chemistry. 4. Epoxidation of p-Methoxy-trans-β[beta]-methylstyrene: An Exercise in NMR and IR Spectroscopy for Sophomore Organic Laboratories

    Rebecca S. Centko and Ram S. Mohan
    Journal of Chemical Education2001 78 (1), 77

    Epoxidation of alkenes using peroxyacids is one of the most fundamental reactions in organic chemistry, yet there are very few examples of laboratory experiments that illustrate this important reaction. We have developed a discovery-oriented lab ...

    Abstract | Hi-Res PDF | PDF w/ Links

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