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Related Experiment Videos

Carbocation-forming reactions in dimethyl sulfoxide.

Xavier Creary1, Elizabeth A Burtch, Ziqi Jiang

  • 1Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA. creary.1@nd.edu

The Journal of Organic Chemistry
|February 1, 2003
PubMed
Summary
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Dimethyl sulfoxide (DMSO) facilitates cationic reactions by forming transient oxosulfonium ions. These intermediates, derived from various organic compounds, react with water to yield alcohol products, demonstrating DMSO

Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms
  • Physical Organic Chemistry

Background:

  • Investigating the reactivity of mesylate derivatives and related compounds in solution.
  • Understanding the role of solvents, particularly dimethyl sulfoxide (DMSO), in mediating chemical transformations.
  • Exploring the mechanisms of reactions involving carbocation intermediates.

Purpose of the Study:

  • To elucidate the reaction pathways of mesylate derivatives and related compounds in DMSO-d(6).
  • To identify and characterize reaction intermediates, particularly oxosulfonium ions.
  • To assess the suitability of DMSO as a solvent for various cationic processes.

Main Methods:

  • First-order kinetic studies in DMSO-d(6).
  • Substituent effect analysis.

Related Experiment Videos

  • H(2)(17)O labeling studies.
  • Spectroscopic characterization of intermediates (e.g., 1-adamantyl mesylate reaction).

    • Main Results:

    • Mesylate derivatives of beta-lactams, thiolactams, and bicyclo[2.2.1]heptanones yield alcohol products via carbocation intermediates and transient oxosulfonium ions in DMSO-d(6).
    • H(2)(17)O labeling confirms oxygen incorporation into DMSO from oxosulfonium ion reactions.
    • Various cationic processes, including elimination and cyclization, were observed with different substrates in DMSO-d(6).
    • 1-Adamantyl mesylate forms a spectroscopically characterized, long-lived oxosulfonium ion in DMSO-d(6).

    Conclusions:

    • DMSO-d(6) effectively promotes cationic reactions by forming and stabilizing oxosulfonium ion intermediates.
    • Trace water in DMSO-d(6) plays a crucial role in product formation by reacting with oxosulfonium ions.
    • DMSO is a versatile solvent for studying and facilitating k(s), k(C), and k(Delta) cationic processes.