Jove
Visualize
Contact Us

Related Experiment Videos

The dimethyldioxirane-mediated oxidation of phenylethyne.

Klaus-Peter Zeller1, Meike Kowallik, Peter Haiss

  • 1Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany. kpz@uni-tuebingen.de

Organic & Biomolecular Chemistry
|July 13, 2005
PubMed
Summary

The oxidation of phenylethyne using dimethyldioxirane yields different products, primarily phenylacetic acid or mandelic acid, depending on reaction conditions like water presence. This study explores reaction pathways and product formation.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Construction of an Internally B3 N3 -Doped Nanographene Molecule.

Angewandte Chemie (International ed. in English)·2015
Same author

Concerning the deprotonation of the trimethylsulfonium ion by the dimethylsulfinyl anion.

Organic & biomolecular chemistry·2011
Same author

Decarbonylation of multi-substituted [18F]benzaldehydes for modelling syntheses of 18F-labelled aromatic amino acids.

Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine·2007
Same author

The photochemical Wolff rearrangement of 3-diazo-1,1,1-trifluoro-2-oxopropane revisited.

Organic & biomolecular chemistry·2003
Same author

A new eudesmane type sesquiterpene from Inula viscosa.

Natural product research·2003
Same author

Flavonoids and terpenoids from the resinous exudates of Madia species (Asteraceae, Helenieae).

Zeitschrift fur Naturforschung. C, Journal of biosciences·2003
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Area of Science:

  • Organic Chemistry
  • Oxidation Reactions
  • Reaction Mechanisms

Background:

  • Dimethyldioxirane (DMDO) is a powerful oxidizing agent.
  • The oxidation of alkynes can lead to various products depending on the reagent and conditions.
  • Understanding reaction pathways is crucial for synthetic chemistry.

Purpose of the Study:

  • To investigate the product distribution of phenylethyne oxidation mediated by dimethyldioxirane.
  • To elucidate the reaction mechanism and the influence of reaction conditions on product formation.
  • To identify key intermediates and their subsequent transformations.

Main Methods:

  • Oxidation of phenylethyne using dimethyldioxirane generated in situ and as pre-formed solutions.
  • Varying reaction conditions, including solvent composition (acetonitrile-water, acetone, tetrachloromethane) and water content.

Related Experiment Videos

  • Analysis of reaction products using standard organic chemistry techniques.

    • Main Results:

    • Product distribution is highly sensitive to reaction conditions, particularly water content.
    • Phenylacetic acid is the major product under in situ conditions in acetonitrile-water.
    • Mandelic acid and oligomeric mandelic acid are favored under anhydrous or low-water conditions.
    • Formation of phenylglyoxylic acid, benzoic acid, and benzaldehyde is also observed and rationalized.

    Conclusions:

    • The reaction proceeds via phenyloxirene, which can rearrange to phenylketene.
    • Water plays a critical role in trapping intermediates, leading to phenylacetic acid or mandelic acid.
    • Anhydrous conditions promote the formation of mandelic acid and its oligomers.
    • Side products arise from further oxidation or degradation pathways of intermediates.