• Login
    View Item 
    •   Oxy Scholar Home
    • Chemistry
    • Chemistry URC Student Scholarship
    • View Item
    •   Oxy Scholar Home
    • Chemistry
    • Chemistry URC Student Scholarship
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Reactions of 2-Bromo-3-Methoxy-1,4-Naphthoquinone with Diaminoalkanes

    Thumbnail
    Author
    Greeson, Azure
    Issue
    urc_student; urc_student
    Date
    2006-01-01 0:00
    Metadata
    Show full item record
    URI
    https://scholar.oxy.edu/handle/20.500.12711/752
    Abstract
    The reactivity of 2-bromo-3-methoxy-1,4-naphthoquinone toward diaminoalkanes is studied here. We reacted 2-bromo-3-methoxy-1,4-naphthoquinone with the following diaminoalkanes: ethylenediamine, 1,3-diaminopropane, N-methylethylenediamine, N-acetylethylenediamine, and 2-aminoethanol. In the reaction of 2-bromo-3-methoxy-1,4-naphthoquinone with ethylenediamine, for example, we isolated 2-2?-aminoethylamino-3-bromo-1,4-naphthoquinone as the major product. We also reacted our starting quinone, 2-bromo-3-methoxy-1,4-naphthoquinone, with the salts of these diaminoalkanes. We expected the salt form of the amine would behave the same as the free amine after the salt?s being freed in the presence of a base. Actually, we found that the freed form of the salt form of some diaminoalkanes produced the product more cleanly in a higher yield. The mechanism for these reactions was also interesting because a substitution occurred at the 3-methoxy site. This is unusual because a bromine atom is a much better leaving group than a methoxy group in a nucleophilic substitution process. We examined a variety of solvents including methanol, ethanol, and chloroform. We also studied the reactions of 3-methoxy-1,4-naphthoquinone with these amines in order to examine the role of the bromine atom in our reaction.
    Collections
    • Chemistry URC Student Scholarship

    Browse

    All of Oxy ScholarCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsJournal TitleJournal IssueThis CollectionBy Issue DateAuthorsTitlesSubjectsJournal TitleJournal Issue

    My Account

    LoginRegister

    DSpace software copyright © 2002-2021  DuraSpace
    Contact Us | Send Feedback
    DSpace Express is a service operated by 
    Atmire NV