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

Egid B. Mubofu; Jan B. F. N. Engberts

doi:10.1002/poc.1240

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 journal › Article › Academic › peer-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 language	English
Pages (from-to)	764-770
Number of pages	7
Journal	Journal of physical organic chemistry
Volume	20
Issue number	10
DOIs	https://doi.org/10.1002/poc.1240
Publication status	Published - 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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title = "Surfactant-assisted specific-acid catalysis of Diels-Alder reactions in aqueous media",

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.",

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",

author = "Mubofu, {Egid B.} and Engberts, {Jan B. F. N.}",

year = "2007",

month = oct,

doi = "10.1002/poc.1240",

language = "English",

volume = "20",

pages = "764--770",

journal = "Journal of physical organic chemistry",

issn = "1099-1395",

number = "10",

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T1 - Surfactant-assisted specific-acid catalysis of Diels-Alder reactions in aqueous media

AU - Mubofu, Egid B.

AU - Engberts, Jan B. F. N.

PY - 2007/10

Y1 - 2007/10

N2 - 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.

AB - 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.

KW - specific-acid catalysis

KW - Diets-Alder reaction

KW - surfactant-type Bronsted acid

KW - micellar catalysis

KW - micellar inhibition

KW - LEWIS-ACID

KW - ORGANIC-REACTIONS

KW - MICELLAR SYSTEMS

KW - FACILE SYNTHESIS

KW - ALDOL REACTIONS

KW - WATER

KW - ALDEHYDES

KW - AMINES

KW - DIENE

KW - ACCELERATION

U2 - 10.1002/poc.1240

DO - 10.1002/poc.1240

M3 - Article

VL - 20

SP - 764

EP - 770

JO - Journal of physical organic chemistry

JF - Journal of physical organic chemistry

SN - 1099-1395

IS - 10

ER -