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Tuesday, 25 March 2014

A solution to fluoronium riddle

The presence of a symmetrical fluoronium ion is confirmed by the 1:1 mixture of reaction products

The first evidence for hypervalent fluorine cations, or fluoronium ions, in solution has been found by US chemists. The research lays the foundations for characterising fluoronium ions – where the fluorine has two bonds and a formal positive charge – directly by spectroscopy and improving our understanding of fluorine’s interactions in organic chemistry

Sunday, 16 March 2014

An efficient Cu(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon-carbon bond formation

An efficient Cu(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon-carbon bond formation

Green Chem., 2014, 16,1470-1479
DOI: 10.1039/C3GC41378K, Paper
Simon Doherty, Julian G. Knight, Jack R. Ellison, Peter Goodrich, Leanne Hall, Christopher Hardacre, Mark J. Muldoon, Soomin Park, Ana Ribeiro, Carlos Alberto Nieto de Castro, Maria Jose Lourenco, Paul Davey
Asymmetric carbon-carbon bond forming reactions were catalysed by heterogeneous copper(II)-bis(oxazoline)-based PIILP systems.

The asymmetric Diels–Alder reaction between N-acryloyloxazolidinone and cyclopentadiene and the Mukaiyama-aldol reaction between methylpyruvate and 1-phenyl-1-trimethylsilyloxyethene have been catalysed by heterogeneous copper(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase (PIILP) systems generated from a range of linear and cross linked ionic polymers. In both reactions selectivity and ee were strongly influenced by the choice of polymer. A comparison of the performance of a range of Cu(II)-bis(oxazoline)-PIILP catalyst systems against analogous supported ionic liquid phase (SILP) heterogeneous catalysts as well as their homogeneous counterparts has been undertaken and their relative merits evaluated.

Saturday, 15 March 2014

Free Download Analysis and Purification Methods in Combinatorial Chemistry

Free Download Analysis and Purification Methods in Combinatorial Chemistry edited by Bing Yan

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Tuesday, 11 March 2014

One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor

Figure 1: Microwave flow reactor for the Bohlmann–Rahtz synthesis of pyridine 2b.

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The Bohlmann–Rahtz pyridine synthesis and the Hantzsch dihydropyridine synthesis can be carried out in a microwave flow reactor or using a conductive heating flow platform for the continuous processing of material. 
In the Bohlmann–Rahtz reaction, the use of a Brønsted acid catalyst allows Michael addition and cyclodehydration to be carried out in a single step without isolation of intermediates to give the corresponding trisubstituted pyridine as a single regioisomer in good yield. 
Furthermore, 3-substituted propargyl aldehydes undergo Hantzsch dihydropyridine synthesis in preference to Bohlmann–Rahtz reaction in a very high yielding process that is readily transferred to continuous flow processing.

Mark C. Bagley1Email of corresponding author, Vincenzo Fusillo2, Robert L. Jenkins2, M. Caterina Lubinu2 andChristopher Mason3
1Department of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton, East Sussex, BN1 9QJ, UK
2School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK
3CEM Microwave Technology Ltd, 2 Middle Slade, Buckingham, MK18 1WA, UK

This article is part of the Thematic Series "Chemistry in flow systems III".
Guest Editor: A. Kirschning
Beilstein J. Org. Chem. 2013, 9, 1957–1968.

Peering Inside Reactors Analytical Chemistry: Microspectroscopy tracks multistep process in action

Reaction scheme shows that a radiation-transparent microreactor allows researchers to look inside to monitor chemical reactions.

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It’s tough to get a detailed account of what’s going on inside catalytic chemical reactors while those workhorse pieces of equipment are running. If researchers could peer inside and monitor—at a microscopic level and in real time—the chemical reactions under way, they would gather a treasure trove of useful information. Engineers could then customize reactor geometry and dimensions and tailor the catalyst distribution to maximize energy efficiency, product output, and chemical selectivity.
That type of custom reactor engineering may be close at hand, thanks to a study conducted by researchers at the University of California, Berkeley, and Lawrence Berkeley National Laboratory.
The team designed a miniature reactor whose interior can be probed microscopically with infrared and X-ray beams. They used it to interrogate a multistep chemical reaction with extreme spatial resolution. The group pinpointed to within 15 μm the regions inside the reactor in which a flowing starting material was transformed to an initial product and then a final product. They correlated that information with the microscopic location, concentration, and chemical state of catalytic nanoparticles (J. Am. Chem. Soc. 2014, DOI: 10.1021/ja412740p).

Wednesday, 5 March 2014

Larvicidal isoxazoles: Synthesis and their effective susceptibility towards Aedes aegypti larvae


Larvicidal isoxazoles: Synthesis and their effective susceptibility towards Aedes aegypti larvae

Volume 21, Issue 4, 15 February 2013, Pages 940–947
Diana C.B. da Silva-Alves, Janaína V. dos Anjos, Nery N.M. Cavalcante, Geanne K.N. Santos, Daniela M.do A.F. Navarro, Rajendra M. Srivastava

 Twenty 3,5-disubstituted isoxazoles have been synthesized and tested against fourth instar Aedes aegyptilarvae. In the synthesis of title compounds, modifications have been made in the C-5 side-chain with a view to test their larvicidal activity. These isoxazoles have been obtained by 1,3-dipolar cycloaddition of arylnitrile oxides to terminal alkynes which furnished the desired products in 20% to 79% yields. A comparative study of the larvicidal activity between 3-(3-aryl-isoxazol-5-yl)-propan-1-ols and 3-(3-aryl-isoxazol-5-yl)-propionic acids clearly demonstrated that the latter compounds possess much better larvicidal activity than the former. We also tested two esters, viz., methyl 3-[3-(phenyl)-isoxazole-5-yl] propionate and methyl 3-[3-(4-chlorophenyl)-isoxazole-5-yl] propionate, where the latter presented an excellent larvicidal profile.