Organic Chemistry Using Weakly Electrophilic Salts:  Efficient Formation of O,O-Mixed, O,S- and N,O-Acetals

• Abstract
• Full Text HTML
• Hi-Res PDF[124 KB]
• PDF w/ Links[233 KB]

• Supporting Info
• Figures
• Citing Articles

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

• PDF/HTML,
  figures/images,
  references and tables,
  (where available)

Abstract

A mild and efficient method for the preparation of O,O-mixed, O,S- and N,O-acetals from symmetrical O,O-acetals has been developed. Thus, the treatment of symmetrical O,O-acetals with TESOTf and 2,4,6-collidine formed weakly electrophilic collidinium salts. The addition of nucleophiles, such as an alcohol, lithium thioxide, and sodium azide, to the salts afforded the corresponding O,O-mixed, O,S- and N,O-acetals in good yields. The reaction proceeded under weakly basic conditions. No overreaction then occurred and many acid-labile functional groups could remain intact.

Citing Articles

View all 13 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 2 ACS Journal articles (2 most recent appear below).

• 

  Expanded Substrate Scope and Improved Reactivity of Ether-Forming Cross-Coupling Reactions of Organotrifluoroborates and Acetals

  Cam-Van Thi Vo , Timothy Andrew Mitchell , and Jeffrey W. Bode
  Journal of the American Chemical Society 0 (ja),

  • Expanded Substrate Scope and Improved Reactivity of Ether-Forming Cross-Coupling Reactions of Organotrifluoroborates and Acetals

    Cam-Van Thi Vo , Timothy Andrew Mitchell , and Jeffrey W. Bode
    Journal of the American Chemical Society 0 (ja),

    Mixed acetals and organotrifluoroborates undergo BF3•OEt2 promoted cross-couplings to give dialkyl ethers under simple, mild conditions. A survey of reaction partners identified a hydroxamate leaving group that improves the regioselectivity and product ...

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

  Mechanistic Pathways in CF₃COOH-Mediated Deacetalization Reactions

  Wei Li, Jianchang Li, Yuchuan Wu, Nathan Fuller and Michelle A. Markus
  The Journal of Organic Chemistry2010 75 (4), 1077-1086

  • Mechanistic Pathways in CF₃COOH-Mediated Deacetalization Reactions

    Wei Li, Jianchang Li, Yuchuan Wu, Nathan Fuller and Michelle A. Markus
    The Journal of Organic Chemistry2010 75 (4), 1077-1086

    It has been widely accepted that both the protection of carbonyls and the deprotection of acetals and ketals involve the participation of a water molecule: formation of acetals and ketals is a dehydration process, whereas the deprotection is often ...

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

SciFinder Links

• Get Reference Detail
• Get Substances
• Get Reactions
• Get Cited
• Get Citing