Selective alkylations of 1,4:3,6-dianhydro-d-glucitol (isosorbide)

Abenhaïm, D.; Loupy, André; Munnier, L.; Tamion, R.; Marsais, Francis; Quéguiner, G.

doi:10.1016/0008-6215(94)84022-9

Cited by 76 publications

(43 citation statements)

References 23 publications

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“…The compounds studied were obtained by sulfation of 2-O-and 5-O-monododecyl isosorbide with Pyr.SO 3 complex. 2-O-and 5-O-monododecyl isosorbide were obtained by direct alkylation of isosorbide by bromododecane as described in references [8,9]. The sulfation route is described below for compound a, and is identical for compound b.…”

Section: Chemicals and General Methodsmentioning

confidence: 99%

“…For each experiment, the data were averaged over two measurements and reproducibility was found to be good. The monododecyl ethers of isosorbide were synthesized by direct alkylation of isosorbide by bromododecane, in the presence of lithium hydroxide in dimethylsulfoxide [8,9]. These reaction conditions promote selectivity towards the 5-O-alkyl isomer due to the higher acidity of proton OH-5 that establishes a hydrogen bond with the oxygen atom of the adjacent cycle (Scheme 1).…”

Section: Foaming Propertiesmentioning

confidence: 99%

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Synthesis and foaming properties of new anionic surfactants based on a renewable building block: Sodium dodecyl isosorbide sulfates

Lavergne

Zhu

Pizzino

et al. 2011

Journal of Colloid and Interface Science

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Section: Chemicals and General Methodsmentioning

confidence: 99%

Section: Foaming Propertiesmentioning

confidence: 99%

Synthesis and foaming properties of new anionic surfactants based on a renewable building block: Sodium dodecyl isosorbide sulfates

Lavergne

Zhu

Pizzino

et al. 2011

Journal of Colloid and Interface Science

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“…[24] Monobenzylated isosorbide and 4-fluoronitrobenzene were reacted in melt in presence of KOH as an alkaline base and 18-Crown-6 as a phase-transfer agent. After precipitation in cold methanol, the nitro compound 1 was isolated as a yellow crystalline powder with high yield (85%).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of novel biosourced building blocks from isosorbide

M'sahel

Elmahdi

Medimagh³

et al. 2016

Designed Monomers and Polymers

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New biosourced unprotected diols were prepared by acylation reaction of aminoalcohol based on 1,4:3,6-dianhydrosorbitol (Isosorbide Is) with several aliphatic and aromatic diacyl chlorides (sebacoyl, adipoyl, and terephthaloyl). Optimization of reaction conditions (solvent, base nature, and addition mode) has been investigated with protected alcohols. The use of hindered bases was needful to ensure the selectivity of the addition reaction when starting from unprotected aminoalcohol, and selectively led to bis amides products with good yields. 1D and 2D NMR techniques were used to ascertain the structures of the unprecedented monomers. These novel building blocks were successfully polymerized using succinic and terephthalic spacers and studied by NMR and DSC techniques.

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“…Eq. (38) In an analogous manner, the selectively obtained exo mono-benzylated isosorbide [58] was alkylated by reaction with alkyl dibromides to afford new ethers from dianhydrohexitols moieties separated by ether functions (Eq. 39 and Tab.…”

Section: Pyrimidine and Purine Derivativesmentioning

confidence: 99%