Surfactant-assisted specific-acid catalysis of Diels-Alder reactions in aqueous media

Egid B. Mubofu*, Jan B. F. N. Engberts

*Corresponding author for this work

    Research output: Contribution to journalArticleAcademicpeer-review

    16 Citations (Scopus)
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    Abstract

    Surfactant-assisted specific-acid catalysis (SASAC) for Diets-Alder reactions of dienophiles 1 and 4 with cyclopentadiene 2 in aqueous media at 32 C was studied. This study showed that acidified anionic surfactants (pH 2) such as sodium dodecyl sulfate (SDS) and linear alkylbenzene sulfonic acid (LAS) accelerate DielsAlder reactions. Conversely, under similar reaction conditions (pH 2) these reactions are inhibited by (acidified) cationic surfactants such as dodecyltrimethylammonium bromide (DTAB), dodecyldimethylammonium bromide (DDAB), and dodecylmethylammonium bromide (DMAB). A modest rate acceleration resulting from the surfactant hydrogen-bonding capacity is also recorded for the Diets-Alder reaction of naphthoquinones (6) with cyclopentadiene (2) in aqueous media at 32 degrees C. Copyright (C) 2007 John Wiley & Sons, Ltd.

    Original languageEnglish
    Pages (from-to)764-770
    Number of pages7
    JournalJournal of physical organic chemistry
    Volume20
    Issue number10
    DOIs
    Publication statusPublished - Oct-2007

    Keywords

    • specific-acid catalysis
    • Diets-Alder reaction
    • surfactant-type Bronsted acid
    • micellar catalysis
    • micellar inhibition
    • LEWIS-ACID
    • ORGANIC-REACTIONS
    • MICELLAR SYSTEMS
    • FACILE SYNTHESIS
    • ALDOL REACTIONS
    • WATER
    • ALDEHYDES
    • AMINES
    • DIENE
    • ACCELERATION

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