ChemInform Abstract: Diels‐Alder Reactions in Micellar Media

Otto, Sijbren; Engberts, Jan B. F. N.

doi:10.1002/chin.200201272

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“…Indeed, a myriad of Lewis acids were employed and brought several outcomes of the Diels-Alder reactions and other cycloaddition reactions such as a stereoselectivity prevalence and an enhancement of the yields and kinetics [26]. Effects that surfactants may confer to the Diels-Alder reactions are: substrate solubilisation, concentration effect, cage effect, preorientation effect, microviscosity effect, and polarity and charge effects [27].…”

Section: General Considerationsmentioning

confidence: 99%

“…Otto and Engberts, and Rispens and Engberts [27,35] made an effort to provide insights into the actual sites of the substrates of Diels-Alder reactions (diene and dienophile) within the micellar media. To this end, they worked out the DA reactions of cyclopentadiene 1, sorbyl alcohol 28, and sorbyltrimethylammonium bromide 29 with a series of N-substituted maleimides 12, 14, 27 (Scheme 6) in micellar media made of surfactants CTAB (cetyltetramethylammonium bromide) and SDS (sodium dodecyl sulfate), at 25 8C.…”

Section: [ ( S C H E M E _ 2 ) T D $ F I G ]mentioning

confidence: 99%

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Cycloaddition reactions in aqueous systems: A two-decade trend endeavor

Moulay

Touati

2010

Comptes Rendus. Chimie

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Cycloaddition reactions are an integral and weighty part of organic chemistry in pedagogy and research as well. The wealthy literature on cycloaddition reactions from their birth up to now, unequivocally witnesses to their leading chemistry. The so-called ''conventional solvents'' are organic solvents that have indubitably promoted their success. Yet, the toxicity facet of these solvents impedes their use freely and with no fear. Not only is the operating chemist uncomfortable while experimenting, but also the environment is equally threatened. Working out the cycloaddition reactions and other organic ones in aqueous systems would certainly bring some relief to the chemist and to the environment as well. Unusual outcomes in terms of yield, reactivity and selectivity compared to those performed in organic solvents were commonly observed, and have overwhelmed the chemists with surprise indeed. In this review, homo Diels-Alder reactions in aqueous media include those involving the following dienophiles: maleimides, a,b-unsaturated esters, p-benzoquinones, vinyl ketones, phenyl-1-(2-pyridyl)-2-propen-1-one, a,bunsaturated esters. A special case is the organocatalysis of Diels-Alder cycloaddition of a,b-unsaturated ketones (aldehydes). Of no less importance, some hetero Diels-Alder cycloaddition reactions in water systems are delineated. The impact of additives (salts, organic and inorganic chemicals), micellar catalysis and Lewis/Brønste ¨d acid catalysis on outcomes of such cycloaddition reactions is discussed. The 1,3-dipolar cycloaddition methodology applied to aqueous media has brought forth a number of heterocyclic compounds, usually with a regio-and stereoselectivity pecularity. These heterocycles include triazoles, tetrazoles, pyrazoles, isoxazoles, isoxazolidines, pyrroles and pyrrolidines. The superiority of copper(I) catalysis in the azide-alkyne cycloaddition (Huisgen cycloaddition) in water is endorsed by a number of examples.

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Section: General Considerationsmentioning

confidence: 99%

Section: [ ( S C H E M E _ 2 ) T D $ F I G ]mentioning

confidence: 99%