Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• locus is hydrophobic and spills out the water into the continuous phase. The ionic liquid 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide was used both as continuous phase and as stabilizer due to its amphiphilic properties. The approach is interesting for synthesizing polymers, which

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• proceeds via nucleophilic attack at the CF3 group with elimination of N,N-dimethylbenzenesulfinamide. The synthetic route to the sulfoximinium salt 42 starts from phenyl trifluoromethyl sulfoxide as depicted in Scheme 35. The triflate salt is an ionic liquid at room temperature whereas the

Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles

• Guillaume G. Launay,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2010, 6, No. 41, doi:10.3762/bjoc.6.41

• noted separately by Jaber et al. [12] and subsequently by Kataoka et al. [13]. For example, homoallylic alcohol 1 was converted to pyran 2 with a high diastereoselectivity (Scheme 1) [12]. Most recently, oxa-, aza- and thia-Prins fluorination cyclisations have been carried out using ionic liquid

• be contrasted with the study using an HF containing ionic liquid (Et4NF·5HF) in place of BF3·OEt2, where diastereoselectivities for similar aza-Prins reactions where around 7:1 to 10:1 in favour of the syn-products [14][15]. The crystal structure of the minor anti-diastereoisomer of the piperidine

1-(4-Alkyloxybenzyl)-3-methyl-1H-imidazol-3-ium organic backbone: A versatile smectogenic moiety

• William Dobbs,
• Laurent Douce and
• Benoît Heinrich

Beilstein J. Org. Chem. 2009, 5, No. 62, doi:10.3762/bjoc.5.62

• William Dobbs Laurent Douce Benoit Heinrich Institut de Physique et Chimie des Matériaux de Strasbourg, UMR 7504, CNRS-Université de Strasbourg, BP 43, 23 rue du Loess, F-67034 Strasbourg Cedex 2, France 10.3762/bjoc.5.62 Abstract The merger of ionic liquid and liquid crystal fields, obtained by

• study of this interesting association led us to elaborate environment-flexible cationic architectures from which mesomorphic properties emerge. Moreover, we have also explored the influence of different anions on the mesomorphic properties. Keywords: crystal liquid; imidazolium salts; ionic liquid

• )sulfonyl]amide), are ionic liquid compounds without any supramolecular organization into mesophase. This is also the case in the series of compounds 5n with n < 12 (only a monotropic mesophase was observed for 512), and finally for 38. Supramolecular arrangement Despite the significant tendency of these

A convenient method for preparing rigid-core ionic liquid crystals

• Julien Fouchet,
• Laurent Douce,
• Benoît Heinrich,
• Richard Welter and
• Alain Louati

Beilstein J. Org. Chem. 2009, 5, No. 51, doi:10.3762/bjoc.5.51

• , differential scanning calorimetry and X-ray diffraction. In addition its lamellar crystal structure, electrochemical behaviour and UV (absorption and emission) properties are reported. Keywords: imidazolium; ionic liquid crystals; Ullman reaction; Introduction Over the past decade extensive studies of ionic

• and fibres. These unique properties lead to their applications ranging from display technology through templating media for synthesis to biological activity (targeting and transporting of drugs and gene materials) [9]. Full convergence of the ionic liquid and liquid crystal fields could provide a vast

• range of materials (Ionic liquid crystals, ILCs) with novel and tunable characteristics such as those of ordered and oriented hybrid compound semiconductors exhibiting both electronic and ionic conductivity [10]. For this, the imidazolium unit is an excellent platform that can be designed to promote

Progress in liquid crystal chemistry

• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 48, doi:10.3762/bjoc.5.48

• diverse topics such as phthalocyanine-fullerene hybrid materials for photovoltaic devices, functional metallomesogens, coaxial electrospinning of liquid crystal-containing microfibers, banana-discotic hybrid systems, ionic liquid crystals, relations between molecular length distribution and formation of

Asymmetric aza-Diels- Alder reaction of Danishefsky's diene with imines in a chiral reaction medium

• Bruce Pégot,
• Olivier Nguyen Van Buu,
• Didier Gori and
• Giang Vo-Thanh

Beilstein J. Org. Chem. 2006, 2, No. 18, doi:10.1186/1860-5397-2-18

• ] Encouraged by this result, we decided to develop asymmetric aza-Diels-Alder reactions of chiral imines with Danishefsky's diene using a chiral ionic liquid as a chiral reaction medium. In our initial studies, we attempt to optimize the conditions for the aza-Diels-Alder reaction between Danishefsky's diene 1

• was observed in the case of p-nitrophenyl (Table 3, entry 4, R = p-NO2C6H4,). This is due to hydrogen bond formation between the OH group of the chiral ionic liquid and the NO2 function of the substrate. A similar decrease in asymmetric induction was observed by our group in the mechanistically

Study of thioglycosylation in ionic liquids

• Jianguo Zhang and
• Arthur Ragauskas

Beilstein J. Org. Chem. 2006, 2, No. 12, doi:10.1186/1860-5397-2-12

• thiomethyl glycosides could readily be activated with methyl trifluoromethane sulfonate, using 1-butyl-3-methylimidazolium tetrafluoroborate as a solvent. This green chemistry glycosylation strategy provided disaccharides with typical yields averaging 75%. The ionic liquid solvent could be readily reused for

• . reported that the glycosidations of glucopyranosyl fluorides with assorted alcohols employing an ionic liquid and a protic acid catalyst proceeded, under mild conditions, to afford the corresponding glycosides in 54–91% yields.[7] The stereoselectivity of the glycosidation was significantly affected by the

• ionic liquid employed. The reactivity of glycosyl trichloroacetimidates and diethyl phosphites with alcohols in the presence and absence of lewis acids has been also recently been reported with several ionic liquids, including [bmim]PF6 and 1-n-hexyl-3-methylimidazolium trifluoromethanesulfonimidide.[8

EcoScale, a semi- quantitative tool to select an organic preparation based on economical and ecological parameters

• Koen Van Aken,
• Lucjan Strekowski and
• Luc Patiny

Beilstein J. Org. Chem. 2006, 2, No. 3, doi:10.1186/1860-5397-2-3

• -evaluated as expensive components. The use of an expensive solvent (e.g. ionic liquid) does not necessarily mean a lower score on the EcoScale, as a higher yield, a better safety profile or easier workup can favourably balance the score. In addition, two special cases can be noted. In a solvent-free