Diels_Alder reactions in water

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

doi:10.1351/pac200072071365

Cited by 199 publications

(137 citation statements)

References 19 publications

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“…43 Detailed examination of aqueous solvent effects on the otherwise solvent-insensitive DA reactions showed that enforced hydrophobic interactions between diene and dienophile and hydrogen bonding of water to the polarised carbonyl moieties in the activated complex play a major role in the large aqueous rate acceleration. 45 The enhanced preference for the endo reaction product (mentioned above) is understood in terms of the smaller solvent accessible surface area for the activated complex leading to this stereoisomer. Computational studies support the interpretation of the beneficial effect of water on these electrocyclic reactions.…”

Section: Diels-alder Reactions In Watermentioning

confidence: 99%

Understanding organic reactions in water: from hydrophobic encounters to surfactant aggregates

2001

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A crucial factor in realising a green chemical process in solution involves the choice of a safe, non-toxic and cheap solvent. Water is the obvious choice. Despite solubility problems, considerable interest has developed recently in organic chemistry in water. This interest also results from the fact that association and chemical reactions often benefit noticeably from the special properties of water, resulting mainly from its small molecular size, its three-dimensional hydrogen-bond network and hydrophobic interactions which are so unique for liquid water. Here we discuss organic reactions and assembly processes in water, largely taken from experiments performed in the authors' laboratories. We show that non-covalent interactions in water can be utilised for fine tuning organic reactions in aqueous media.

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Section: Diels-alder Reactions In Watermentioning

confidence: 99%

Understanding organic reactions in water: from hydrophobic encounters to surfactant aggregates

2001

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“…Diels-Alder reactions have been studied as powerful chemical reactions to be used in high-yield and high-stereoselective methods [2][3]. The 1,3-dipolarcycloaddition reaction, one of the well-known Dields-Alder reactions, requires each reactant to have a high-diffusion coefficient within one phase in multiple phase systems, although most of the substrates are hydrophobic and are not readily dissolved in the water phase.…”

Section: Introductionmentioning

confidence: 99%

Partitioning of Hydrophobic Molecules to Liposome Membranes Can Induce Variations in their Micro-Polarity and Micro-Viscosity

Iwasaki

Suga

Kondo

et al. 2015

SERDJ

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The micro-polarity and micro-viscosity of liposome membranes were evaluated to develop a platform for the localization of hydrophobic substrates in aqueous solution. The distribution ratios of benzaldoxime (BO) onto the zwitterionic 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) liposome and onto the cationic 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP) liposome were almost the same, while those of benzonitrile oxide (BNO) onto DOTAP liposomes were higher than those of BO. Through the analysis of a polarity-sensitive 6-lauroyl-2-dimethylaminonaphthalene, the membrane surface of the DOTAP liposome was found to be dehydrated in the presence of substrates. Using a fluorescent probe 1,6-diphenyl-1,3,5-hexatriene, we found that the micro-viscosity of the DOTAP liposome membrane increased with BNO. These results indicate that the interaction of hydrophobic substrates induce variations in the microscopic membrane environment.

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“…Water as a reaction medium has gained importance in the development of sustainable chemistry. 52 As a common catalyst for phase transfer, cetyltrimethyl ammonium bromide (CTAB is able to expedite the reaction between anion or nucleophile and neutral substrate via transferring one phase to another, making them collided with each other frequently. 53 In continuation of our efforts to develop green synthetic routes for the formation of C-C and carbon-heteroatom bond, 54 we herein report a green, simple and practical method for the synthesis of 2-sustituted benzothiazoles from the condensation of 2-aminothiophenol with aldehydes catalyzed by CTAB in water.…”

Section: Introductionmentioning

confidence: 99%

Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by cetyltrimethyl ammonium bromide (CTAB) in water

Yang¹,

Xu²,

Lin³

et al. 2010

J. Braz. Chem. Soc.

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Uma série de benzotiazóis 2-substituídos foi sintetizada pela condensação de 2-aminotiofenol com aldeídos (RCHO: R = Alquil, Aril, Heteroaril, 2-Arilformil) na presença de quantidade catalítica de brometo de cetiltrimetil amônio (CTAB) em água e sem adição de solventes orgânicos e oxidantes. Assim, usando esse protocolo, 2-alquilbenzotiazóis foram sintetizados em altos rendimentos e 2-arilformilbenzotiazóis foram obtidos pela condensação de 2-aminotiofenol com arilformil aldeídos pela primeira vez.A series of 2-substituted benzothiazoles have been synthesized by the condensation of 2-aminothiophenol with aldehydes (RCHO: R = Alkyl, Aryl, Heteroaryl, 2-Arylformyl) in the presence of a catalytic amount of cetyltrimethyl ammonium bromide (CTAB) "on water" by a onepot procedure without additional organic solvents and oxidants. Thereinto, 2-alkylbenzothiazoles were synthesized in high yields and 2-arylformylbenzothiazoles were obtained from the condensation of 2-aminothiophenol with arylformyl aldehydes for the first time using the present protocol.

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Diels_Alder reactions in water

Cited by 199 publications

References 19 publications

Understanding organic reactions in water: from hydrophobic encounters to surfactant aggregates

Understanding organic reactions in water: from hydrophobic encounters to surfactant aggregates

Partitioning of Hydrophobic Molecules to Liposome Membranes Can Induce Variations in their Micro-Polarity and Micro-Viscosity

Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by cetyltrimethyl ammonium bromide (CTAB) in water

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