Skip to main content
SpringerLink
Log in

The Enantiomers of Spiro(cyclohexadiene-indolines) and their Thermal Racemization

Die Enantiomeren von Spiro(cyclohexadien-indolinen) und ihre thermische Racemisierung

  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

 The separation of the enantiomers of substituted spiro(cyclohexadiene-indolines) was performed by enantioselective liquid chromatography with the sorbent/solvent systems triacetylcellulose/methanol, triacetylcellulose/ethanol/water, and (+)-poly(trityl methacrylate)/SiO2/n-hexane/isopropanol. The interconversion barriers of the enantiomers were determined for a series of derivatives by thermal racemization. A mechanism for the thermal ring opening/ring closure is discussed in terms of the Woodward-Hoffmann rules.

Zusammenfassung.

 Die Enantiomeren von substituierten Spiro(cyclohexadien-indolinen) wurden durch enantioselektive Flüssigkeitschromatographie mit den Solvent/Sorbens-Systemen Triacetylcellulose/Methanol, Triacetylcellulose/Ethanol/Wasser und (+)-Poly(tritylmethacrylat)/SiO2/n-Hexan/Isopropanol getrennt. Aus thermischen Racemisierungen wurden die Barrieren der Enantiomerisierung für eine Reihe von Derivaten bestimmt. Ein Mechanismus der thermischen Ringöffnung und des Ringschlusses wird auf der Grundlage der Woodward-Hoffmann-Regeln diskutiert.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Author information

Authors and Affiliations

  1.  Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Federal Republic of Germany, DE

    Thomas Zimmermann

  2.  Institut für Organische Chemie, Universität Leipzig, D-04303 Leipzig, Federal Republic of Germany, DE

    Nikola Pustet & Albrecht Mannschreck

Authors
  1. Thomas Zimmermann
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nikola Pustet
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Albrecht Mannschreck
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Received August 31, 1998. Accepted September 9, 1998

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zimmermann, T., Pustet, N. & Mannschreck, A. The Enantiomers of Spiro(cyclohexadiene-indolines) and their Thermal Racemization. Monatshefte fuer Chemie 130, 355–361 (1999). https://doi.org/10.1007/PL00010217

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/PL00010217

Search

Navigation