Chlorotrimethylsilane:  A Suitable Reagent for the Synthesis of Chlorohydrin Esters

Eras, Jordi; Méndez, Jonh Jairo; Balcells, Mercè; Canela, Ramón

doi:10.1021/jo026020w

Cited by 23 publications

(11 citation statements)

References 32 publications

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“…Afterwards, this compound could react with halogen ions present in the medium through a nucleophilic opening process similar to the one proposed by several authors. 17,[24][25][26][27] Although the detailed catalytic function of ILs is not clear at this stage, the preliminary experimental results showed that bromoesterificaction in ILs is not only possible but also satisfactory. Moreover, polarity and H-bonding capability of the IL could have a big influence in the reaction behavior.…”

Section: Resultsmentioning

confidence: 96%

“…The need for similar assistance has already been proposed by several authors to explain similar processes. 17,24,25 A feasible mechanism is outlined in Fig. 2.…”

Section: Resultsmentioning

confidence: 99%

“…Diol could be transformed into the monoesters followed by the formation of a dioxygenated ring (7,8), similar to those proposed by several authors. 3,17,[24][25][26][27][28] These intermediates, in equilibrium with the open monoester, can tautomerize to 9. Afterwards, this compound could react with halogen ions present in the medium through a nucleophilic opening process similar to the one proposed by several authors.…”

Section: Resultsmentioning

confidence: 99%

“…These results are in concordance with those described by Eras et al in which the halohydrin ester having the halogen in the primary position was mainly formed. 17 Apart from a,b-bromooctyl palmitates, small amounts of hydroxyoctyl palmitates, 1,2-octanediol dipalmitates and bromooctanols were also obtained. However, the bromohydrin esters (3a, 4a) are easily purified using silica column chromatography.…”

Section: General Proceduresmentioning

confidence: 99%

“…The method consist in one-pot esterification-chlorination reaction, in which chlorotrimethylsilane acts as a solvent, catalyzer and chlorine source. 17 Trying to avoid the use of chlorotrimethylsilane, our work was focused on developing a new friendly one-pot halohydrin ester synthesis using potassium halides (KX) as halogen source in ionic liquids (ILs). ILs are a greener alternative to volatile organic solvents and their solvent properties may be easily controlled by altering the nature of their cations and anions.…”

Section: Introductionmentioning

confidence: 99%

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[BMIM][PF6] Promotes the Synthesis of Halohydrin Esters from Diols Using Potassium Halides

et al. 2008

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Haloesterification of diverse diols with various carboxylic acids was achieved using potassium halides (KX) as the only halide source in ionic liquids. The best yield was obtained in [BMIM][PF6] when 1,2-octanediol, palmitic acid and KBr were used. This yield was 85% and the regioisomer with the bromine in primary position was present in a 75:25 ratio. The regioisomeric ratio could be improved using either KCl or some phenylcarboxylic acids. [BMIM][PF6] acts as both reaction media and catalyst of the reaction. To the best of our knowledge, this type of combined reaction using an ionic liquid is unprecedented. The other solvents tested did not lead either to the same yield or to the same regioisomeric ratio.

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Section: Resultsmentioning

confidence: 96%

“…The need for similar assistance has already been proposed by several authors to explain similar processes. 17,24,25 A feasible mechanism is outlined in Fig. 2.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: General Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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[BMIM][PF6] Promotes the Synthesis of Halohydrin Esters from Diols Using Potassium Halides

et al. 2008

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Intermolecular Halogenation/Esterification of Alkenes with N‐Halosuccinimide and Acetic Acid Catalyzed by 1,4‐Diazabicyclo[2.2.2]octane

2017

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Abstract1,4‐Diazabicyclo[2.2.2]octane (DABCO) is a suitable Lewis base that acts as an organocatalyst in the activation of N‐chlorosuccinimide (NCS) towards the chlorination of alkenes. The chloriranium ion formed from NCS and the alkene, can be intermolecularly opened by a nucleophile, such as acetic acid, to produce highly functionalized trans‐chloro esters in high yields. The protocol is also applied to the synthesis of chlorohydrins and chloro ethers using water or methanol as nucleophiles instead of acetic acid. Brominated analogs can also be synthesized from alkenes and N‐bromosuccinimide (NBS) in the presence of various basic catalysts. However, the reaction patterns seem to be remarkably different. The catalytic performance of bases in the bromoesterification of alkenes was found to be strongly affected by their Brønsted basicity, suggesting that acetyl hypobromite, formed in situ from NBS and acetic acid, acts as a real brominating agent in these systems.magnified image

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Solvent free biocatalytic synthesis of vinyl monomers by lipase immobilized on hydrogels

Chauhan

Kanwar

Kumar

et al. 2008

J of Applied Polymer Sci

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Simple novel research plan has been employed to tailor supports for lipase immobilization. N-aminoethylacrylamide (N-AEAAm) and N-aminoethylmethacrylamide (N-AEMAAm) were crosslinked with N,N-methylene bisacrylamide (N,N-MBAAm) and consequently reacted separately with acrylic acid (AAc) and methacrylic acid (MAAc). The hydrogels thus formed, consist of both amide and carboxylic functional groups. These hydrogels were characterized by nitrogen analysis, SEM, FTIR and also by water uptake studies as a function of time, temperature, pH, and the presence of additives like sodium dodecyl sulfate (SDS) and cetyl trimethyl ammonium bromide (CTAB). These hydrogels are environmentally sensitive. In the presence of surfactants, these hydrogels show micellization and swell to the maximum at the critical micellar concentration (CMC) of the surfactants. Lipase was immobilized on these hydrogels and the one exhibiting the maximum activity was further used as biocatalyst to explore nonconventional green routes for the synthesis of some known and novel vinyl monomers. Yields obtained have been high and the immobilized lipase show high reusability.

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Chlorotrimethylsilane: A Suitable Reagent for the Synthesis of Chlorohydrin Esters

Cited by 23 publications

References 32 publications

[BMIM][PF6] Promotes the Synthesis of Halohydrin Esters from Diols Using Potassium Halides

[BMIM][PF6] Promotes the Synthesis of Halohydrin Esters from Diols Using Potassium Halides

Intermolecular Halogenation/Esterification of Alkenes with N‐Halosuccinimide and Acetic Acid Catalyzed by 1,4‐Diazabicyclo[2.2.2]octane

Solvent free biocatalytic synthesis of vinyl monomers by lipase immobilized on hydrogels

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