Synthesis and characterization of N-1-(4-toluenesulfonyl)-N-1-(9-anthracenemethyl)triamines

    Authors

    C. J. Wang; K. A. Abboud;O. Phanstiel

    Comments

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    Abbreviated Journal Title

    J. Org. Chem.

    Keywords

    TRANSPORT; HOMOLOGATION; SPERMINE; ANALOGS; Chemistry, Organic

    Abstract

    A modular synthetic approach was developed to access triamines with varying tether lengths from commercially available aminoalkanols. Initial N-alkylation via reductive amination with anthracene-9-carbaldehyde provided the secondary amines in good yield. Subsequent ditosylation with excess TsCl yielded the respective bis-N,O-tosylates. The tosylates were reacted with excess putrescine to give the final triamines. X-ray crystallography revealed that the polyamine tail is preferentially oriented over the shielding cone of the anthracene ring.

    Journal Title

    Journal of Organic Chemistry

    Volume

    67

    Issue/Number

    22

    Publication Date

    1-1-2002

    Document Type

    Article

    Language

    English

    First Page

    7865

    Last Page

    7868

    WOS Identifier

    WOS:000178820200041

    ISSN

    0022-3263

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