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Issue 8 of Green Chemistry now online

The latest issue of Green Chemistry is now available online!

The front cover of issue 8 features work by Matthew Fuchter and co-workers from Imperial College London and Pfizer Ltd in Sandwich.  The team developed a route to give allylic alcohols from α,β-unsaturated ketones using calcium triflate to replace cerium(III) chloride.  This procedure also accomplished the regioselective 1,2-reduction of challenging α,β-unsaturated ketones such as 2-cyclopentenone with very good selectivity, and is suitable for the stereoselective reduction of α,β-aziridinyl ketones.

Lanthanide replacement in organic synthesis: Luche-type reduction of α,β-unsaturated ketones in the presence of calcium triflate, Nina V. Forkel, David A. Henderson and Matthew J. Fuchter, Green Chem., 2012, 14, 2129-2132.

The inside front cover highlights work by Man Bock Gu and colleagues from Korea University in Seoul, who report the carbonic anhydrase-assisted formation of biomineralized calcium carbonate crystalline composites (CCCCs).  These materials were shown to be effective biocatalysts retaining 43% of the free carbonic anhydrase esterase activity.  The catalysts were stable for more than 50 days at room temperature, could be recovered easily using magnet-based separation and retained their activity over 10 repeated usages.

Carbonic anhydrase assisted calcium carbonate crystalline composites as a biocatalyst, Ee Taek Hwang, Haemin Gang, Jinyang Chung and Man Bock Gu, Green Chem., 2012, 14, 2216-2220

These articles are free to access for 6 weeks

Keep up-to-date with the latest content in Green Chemistry by registering for our free table of contents alerts!

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Top ten most accessed articles in June

This month sees the following articles in Green Chemistry that are in the top ten most accessed:-

Catalytic conversion of biomass using solvents derived from lignin
Pooya Azadi, Ronald Carrasquillo-Flores, Yomaira J. Pagán-Torres, Elif I. Gürbüz, Ramin Farnood and James A. Dumesic
Green Chem., 2012,14, 1573-1576, DOI: 10.1039/C2GC35203F, Communication

An efficient copper-catalyzed formation of highly substituted pyrazoles using molecular oxygen as the oxidant
Mamta Suri, Thierry Jousseaume, Julia J. Neumann and Frank Glorius
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35476D, Paper

Multicomponent reactions in unconventional solvents: state of the art
Yanlong Gu
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35635J, Critical Review

Selective conversion of microcrystalline cellulose into hexitols on nickel particles encapsulated within ZSM-5 zeolite
Guanfeng Liang, Haiyang Cheng, Wei Li, Limin He, Yancun Yu and Fengyu Zhao
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35685F, Communication

An efficient protocol for palladium-catalyzed ligand-free Suzuki-Miyaura coupling in water
Manoj Mondal and Utpal Bora
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35401B, Communication

Evolution of asymmetric organocatalysis: multi- and retrocatalysis
Raffael C. Wende and Peter R. Schreiner
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35160A, Critical Review

TBHP/I2-promoted oxidative coupling of acetophenones with amines at room temperature under metal-free and solvent-free conditions for the synthesis of a-ketoamides
Xiaobin Zhang and Lei Wang
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35489F, Communication

Copper-catalyzed reductive amination of aromatic and aliphatic ketones with anilines using environmental-friendly molecular hydrogen
Svenja Werkmeister, Kathrin Junge and Matthias Beller
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35565E, Communication

A simple and facile Heck-type arylation of alkenes with diaryliodonium salts using magnetically recoverable Pd-catalyst
Buchi Reddy Vaddula, Amit Saha, John Leazer and Rajender S. Varma
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35673B, Communication

Efficient catalytic hydrogenation of levulinic acid: a key step in biomass conversion
József M. Tukacs, Dávid Király, Andrea Strádi, Gyula Novodarszki, Zsuzsanna Eke, Gábor Dibó, Tamás Kégl and László T. Mika
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35503E, Paper

Why not take a look at the articles today and blog your thoughts and comments below.

Fancy submitting an article to Green Chemistry? Then why not submit to us today or alternatively email us your suggestions.

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Putting Green Chemistry into Mobile Apps to Communicate Globally

Screenshot of the Green Solvents App for iPad

Screenshot of the Green Solvents App for iPad

Several new mobile applications (Apps) have been recently released for the Apple iOS platform which incorporate green chemistry concepts. This represents a highly novel way to communicate science and bring green chemistry to a bigger audience, which has not previously been appreciated. We certainly sense there is an untapped audience for these types of applications due to the large number of people who now own a mobile device across all demographics. Green Chemistry related information is generally proprietary and papers on the topic are commonly behind paywalls. Making the information freely available or at low cost is a paradigm shift.

For example, a recent consortium organized by the American Chemical Society Green Chemistry InstituteTM (ACS GCI) Pharmaceutical Roundtable1 currently involves 14 pharmaceutical companies, and has developed a solvent selection guide that is publicly available on their website in the form of a PDF file.2 We have made this solvent selection guide more accessible in the form of a free app called Green Solvents.3, 4 It is delivered as a simple structure look-up guide incorporating all of the selection criteria from the ACS GCI and, in addition, having links out to other useful resources (ChemSpider 5-7 etc.). This app, like most free apps, has a small banner advertisement which does not detract from the content of the app or its usability on a mobile device. Importantly this App was not funded by the ACS or any other organization.

Screenshot of the Open Drug Discovery Teams App for iPad

Screenshot of the Open Drug Discovery Teams App for iPad

Creating the Green Solvents app has also motivated the addition of the process mass intensity (PMI) calculation8 (which is another green chemistry feature), into the Yield101 app9. A third recently developed mobile app connected to green chemistry is the Open Drug Discovery Teams (ODDT) app10, 11. ODDT is a free mobile app intended as a research topic aggregator of science data collected from various sources on the internet such as Twitter and Google Alerts. It exists to facilitate interdisciplinary teamwork and deliver access to information that is highly relevant and focused on the topic areas of interest. Research topics include areas of chemistry and adjacent molecule-oriented biomedical sciences, with an emphasis on those which are most amenable to open research at present. We have focused on green chemistry as a topic due to its potential importance for scientists involved in drug discovery for rare and neglected diseases. There is high attrition in drug discovery, so many compounds will need to be made but only a very small fraction will make it into the clinic and, far less, into the marketplace. It is therefore important to design a green process as early as possible when the cost is lower and the quantities of chemicals made are relatively small compared to when they are dramatically scaled up for manufacturing. We feel these global neglected and rare disease researchers would benefit greatly from being informed about green chemistry principles early on and that this has not been considered by any of the major organizations driving green chemistry initiatives. This app has also been used to visualize the ACS GCI solvent selection guide in a different format as it was Tweeted out to reach an even wider audience for those following the hashtag #greenchemistry. To date we are the only researchers that have created and used mobile apps to communicate green chemistry concepts. We feel this is an area that is ripe for expansion to further educate scientists.

Sean Ekins*
Collaborations in Chemistry, 5616 Hilltop Needmore Road, Fuquay-Varina, NC 27526, U.S.A.
Alex M. Clark
Molecular Materials Informatics, 1900 St. Jacques #302, Montreal, Quebec, Canada H3J 2S1
Antony J. Williams
Royal Society of Chemistry, 904 Tamaras Circle, Wake Forest, NC 27587, U.S.A. 

1. American Chemical Society Green Chemistry InstituteTM Pharmaceutical Roundtable www.acs.org/gcipharmaroundtable
2. Solvent selection guide. http://surveys.acs.org/se.ashx?s=04BD76CC0E5496A7
3. Ekins, S. Green Solvents: From Idea to App in 3 Days. http://www.slideshare.net/ekinssean/green-solvents-app
4. Clark, A. M. Green Solvents. http://www.scimobileapps.com/index.php?title=Green_Solvents
5. ChemSpider. www.chemspider.com
6. Pence, H. E.; Williams, A. J. ChemSpider: An Online Chemical Information Resource. J Chem Educ 2010, 87, 1123-1124.
7. Williams, A. J. Public chemical compound databases. Curr Opin Drug Discov Devel 2008, 11, 393-404.
8. ACS GCI Pharmaceutical Roundtable. http://portal.acs.org/portal/acs/corg/content?_nfpb=true&_pageLabel=PP_TRANSITIONMAIN&node_id=1422&use_sec=false&sec_url_var=region1&__uuid=46aca9b6-a985-42cd-a534-7d6cabf892a7
9. Clark, A. M. Yield-101. http://www.scimobileapps.com/index.php?title=Yield101
10. Ekins, S.; Clark, A. M.; Williams, A. J. Open Drug Discovery Teams: A Chemistry Mobile App for Collaboration. Molecular Informatics 2012, In Press.
11. Philippidis, A. App connects rare disease researchers to data. http://www.genengnews.com/insight-and-intelligenceand153/app-connects-rare-disease-researchers-to-data/77899637/

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Green Chemistry celebrates highest ever impact factor – 6.32

The release of the 2011 Thomson Scientific (ISI) Journal Citation Reports* sees Green Chemistry achieve an impact factor over 6 for the first time! 

The 2011 impact factor of 6.32 re-enforces Green Chemistry’s position as one of the leading Journals in the field of sustainable chemistry and technology.

We would like to thank all our authors, referees, readers and Editorial and Advisory Board  members for their help and support on the Journal.

Join your colleagues and submit your research today!

Read more about the 2011 Impact Factors from across RSC Publishing on the RSC Publishing Blog.

*The Impact Factor provides an indication of the average number of citations per paper. Produced annually, Impact Factors are calculated by dividing the number of citations in a year, by the number of citeable articles published in the preceding two years. Data based on 2011 Journal Citation Reports®, (Thomson Reuters, 2012).

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Green Chemistry issue 7 – now online!

The latest issue of Green Chemistry is now available online and is packed with the usual high quality research.

The front cover of this issue showcases the Critical Review by Raffael Wende and Peter Schreiner from Justus-Liebig University in Giessen, Germany, on the evolution of asymmetric organocatalysis.  The authors focus on the recent developments into organomulticatalysis, i.e.the combination of several distinct organocatalysts enabling consecutive reactions to be conducted in one pot. Schreiner and Wende also look at multicatalysts – catalysts with a single backbone with several independent, orthogonally reactive moieties attached.  The review highlights the impressive advantages of asymmetric organomulticatalysis and look at the development that have occurred from it’s very beginnings to the latest multicatalyst systems. 

Evolution of asymmetric organocatalysis: multi- and retrocatalysis, Raffael C. Wende and Peter R. Schreiner, Green Chem., 2012, 14, 1821-1849

The inside front cover highlights work by Hong Liu and colleagues from the Shanghai Institute of Materia Medica, Chinese Academy of Sciences, China, who reported the gold catalysed synthesis of fused polycyclic indoles.  Substituted 2-(1H-indol-1-yl)alkylamines were reacted with alkynoic acids in water under microwave irradiation for 30 min giving the products in excellent yields.  This procedure proceeds with high atom economy and leads to the generation of two rings, together with the formation of one new C-C bond and two new C-N bonds in a single operation. 

Gold-catalyzed tandem reaction in water: an efficient and convenient synthesis of fused polycyclic indoles, Enguang Feng, Yu Zhou, Fei Zhao, Xianjie Chen, Lei Zhang, Hualiang Jiang and Hong Liu, Green Chem., 2012, 14, 1888-1895

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Top ten most accessed articles in May

This month sees the following articles in Green Chemistry that are in the top ten most accessed:-

Iron-catalyzed arylation of benzoazoles with aromatic aldehydes using oxygen as oxidant
Saiwen Liu, Ru Chen, Xiangyu Guo, Huiqiong Yang, Guojun Deng and Chao-Jun Li
Green Chem., 2012,14, 1577-1580, DOI: 10.1039/C2GC35457H, Communication

Evolution of asymmetric organocatalysis: multi- and retrocatalysis
Raffael C. Wende and Peter R. Schreiner
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35160A, Critical Review

Triacetic acid lactone as a potential biorenewable platform chemical
Mei Chia, Thomas J. Schwartz, Brent H. Shanks and James A. Dumesic
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35343A, Communication

An efficient protocol for palladium-catalyzed ligand-free Suzuki-Miyaura coupling in water
Manoj Mondal and Utpal Bora
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35401B, Communication

Efficient catalytic hydrogenation of levulinic acid: a key step in biomass conversion
József M. Tukacs, Dávid Király, Andrea Strádi, Gyula Novodarszki, Zsuzsanna Eke, Gábor Dibó, Tamás Kégl and László T. Mika
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35503E, Paper

Solvent- and catalyst-free synthesis of new hydroxylated trisubstituted pyridines under microwave irradiation
Guodong Yin, Qiong Liu, Junrui Ma and Nengfang She
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35243E

Construction of a quinoline ring via a 3-component reaction in water: crystal structure analysis and H-bonding patterns of a 2-aryl quinoline
T. Ram Reddy, L. Srinivasula Reddy, G. Rajeshwar Reddy, Kaviraj Yarbagi, Y. Lingappa, D. Rambabu, G. Rama Krishna, C. Malla Reddy, K. Shiva Kumar and Manojit Pal
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35256G, Communication

The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts
Ricardo Alamillo, Mark Tucker, Mei Chia, Yomaira Pagán-Torres and James Dumesic
Green Chem., 2012,14, 1413-1419, DOI: 10.1039/C2GC35039D, Paper

Simultaneous delignification and selective catalytic transformation of agricultural lignocellulose in cooperative ionic liquid pairs
Jinxing Long, Xuehui Li, Bin Guo, Furong Wang, Yinghao Yu and Lefu Wang
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35105F, Paper

“On water” direct Pd-catalysed C-H arylation of thiazolo[5,4-d]pyrimidine derivatives
Ye-Xiang Su, Ya-Hui Deng, Ting-Ting Ma, Yu-Yan Li and Li-Ping Sun
Green Chem., 2012, Advance Article, DOI: 10.1039/C2GC35399G, Paper

Why not take a look at the articles today and blog your thoughts and comments below.

Fancy submitting an article to Green Chemistry? Then why not submit to us today or alternatively email us your suggestions.

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Lanthanide replacement in organic synthesis

Scientists form the UK have performed the Luche-type reduction of α,β-unsaturated ketones in the presence calcium triflate.

The reduction of α,β-unsaturated ketones to synthesize allylic alcohols is commonly performed with sodium borohydride in the presence of cerium(III) chloride, otherwise known as the Luche reduction.  However, trivalent lanthanide salts pose several disadvantages.  They are very expensive, and although generally non-toxic, if administered intravenously they are significantly toxic.

However, in this work scientists from Imperial College London and Pfizer Ltd in Sandwich, led by Matthew Fuchter, developed a route to give allylic alcohols from α,β-unsaturated ketones using calcium triflate to replace cerium(III) chloride.  This procedure also accomplished the regioselective 1,2-reduction of challenging α,β-unsaturated ketones such as 2-cyclopentenone with very good selectivity, and is suitable for the stereoselective reduction of α,β-aziridinyl ketones.

This article is free to access until the 23rd July 2012!  Click on the link below to find out more…

Lanthanide replacement in organic synthesis: Luche-type reduction of α,β-unsaturated ketones in the presence of calcium triflate, Nina V. Forkel, David A. Henderson and Matthew J. Fuchter, Green Chem., 2012, DOI: 10.1039/C2GC35619H

You may also be interested in these articles – free to access for 2 weeks:

Effective synthesis of 2,5-disubstituted tetrahydrofurans from glycerol by catalytic alkylation of ketones, Magnus Rueping and Vilas B. Phapale, Green Chem., 2012, 14, 55-57

Environmentally benign metal triflate-catalyzed reductive cleavage of the C–O bond of acetals to ethers, Yin-Jie Zhang, Wissam Dayoub, Guo-Rong Chen and Marc Lemaire, Green Chem., 2011, 13, 2737-2742

Stay up-to-date with the latest content in Green Chemistry by registering for our free table of contents alerts.

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Faster removal of cigarette filters from the environment

Cigarette filters that have been inappropriately discarded are a major environmental problem, making up a large proportion of litter, as the filters themselves can take years to degrade. In a bid to tackle this, researchers in the US have developed a cigarette filter with accelerated degradation.

Raymond Robertson from the acetate business of Celanese Corporation, Narrows, Virginia, has been working with colleagues to develop a filter that contains a controlled-release organic acid to catalyse the hydrolysis of the filter material – cellulose acetate polymer. ‘Our work focuses on expediting the filter degradation back to cellulose and acetic acid using edible materials, such as citric acid and ascorbic acid (vitamin C), to help promote the filter degradation rate,’ he says. ‘Increasing the degradation rate decreases the filter persistence in the environment.’

The weak organic acid is encapsulated in the filter paper to protect it from premature degradation and to prevent a decrease in the product’s shelf life. Once the cigarette is used and discarded, environmental water (such as rainwater) breaches the protective layer. This releases the acid, which migrates into the filter, lowering the pH and triggering hydrolysis.

Zhenjiang Li from Nanjing University of Technology, China, comments: ‘It is a remarkable breakthrough in addressing the cigarette filter pollution.’ A researcher in the fields of green chemistry and polymers, Li is impressed with the results. ‘The team have combined simple chemistry with current industrial processes.’

For Robertson, future developments involve refining the technology to suit a variety of environments, such as developing a coating and release technology that can work in very wet conditions.

Reproduced from a Chemistry World story written by Rebecca Brodie

This article is free to access for 6 weeks!  Click on the link below to find out more…

Accelerated degradation of cellulose acetate cigarette filters using controlled-release acid catalysis, Raymond M. Robertson, William C. Thomas, Jitendrakumar N. Suthar and David M. Brown, Green Chem., 2012, DOI: 10.1039/C2GC16635F

Stay up-to-date with the latest content in Green Chemistry by registering for our free table of contents alerts.

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Meet our Authors – Andrew Abbott

Andrew Abbott is a Professor of Physical Chemistry and Head of the Department of Chemistry at the University of Leicester, UK.  His research is based on the design, fundamental studies and applications of ionic liquids and deep eutectic solvents.  Andy took a few moments to chat to Green Chemistry

Who or what initially inspired you to become a chemist?

As with most chemists, I can trace my career in Chemistry to my chemistry teacher at school, Mr David Peacock at Abbotsfield School, West London. He used to take us to all kinds of demonstration lectures and he was a great inspiration.

What has been the motivation behind your recent research?

My own research is in the area of sustainable solvents, particularly ionic liquids. I am interested in developing sustainable materials and we are focussing on metal deposition and dissolution which I feel are some of the most pressing issues in green chemistry. Reducing aqueous effluents of heavy metals are some of the most pressing issues because of the acute toxicity and large volumes of the processes. These are ubiquitous problems and all of the solutions tend to be end of pipe. Our approach is to use ionic media to avoid aqueous effluent. This also allows us to build in more energy efficient deposition processes. We have take a number of these to commercial scale. We produce our liquid systems with the catch phrase “benign by design”. We ensure that rather than looking for the perfect chemical system we start with the perfect environmental system and then tailor it to the application. Our work is also investigating novel starch based plastics building biodegradation in from the outset and attempting to modify to material to obtain the optimum mechanical properties.

What do you see as the main challenges facing research in this area?

The main challenge facing Green Chemistry is the conservative tendency in manufacturing which leads to small incremental change. The challenge from an academic point of view is retaining credibility for new technologies. We still tend to go in fads such as supercritical fluids or ionic liquids and see them as a panacea. Process design tends to be lacking from many approaches. There is also a tendency to claim that something is Green as if it is an absolute that can be achieved. We need to focus on relative improvements in green metrics.

Where do you see the field of Green Chemistry being in 5 or 10 years time?

One of the challenges in Green Chemistry over the next 10 years is retaining credibility and building successful case studies. It should be seen as a goal in all processes to improve the green metrics and it should be a key goal to develop simple criteria that are non-quantitative but are highly indicative of the relative improvements that a process makes over existing technology. A simple scale or traffic light scheme which quantified changes in key indicators such as the scale of the process, the relative change in the hazard, environmental impact, and the practicality of the methodology.

And finally…

If you could not be a scientist, but could be anything else, what would you be?

Chemistry was always my fallback position. I always wanted to be an artist and had it not been for my lack of talent I would have surely made it. Recently I fulfilled a personal challenge to combine both areas and I devised a public lecture on the chemists role in art entitled “From Test Tube to Turner” which I gave at Burlington House. Even in this lecture there is still some Green Chemistry where I discuss the chemists desire to remove toxic heavy metals from the artists palette.

A couple of Andy’s recent Green Chemistry articles are currently free to access until the 18th July 2012:

Salt modified starch: sustainable, recyclable plastics, Andrew P. Abbott, Andrew D. Ballantyne, Jesus Palenzuela Conde, Karl S. Ryder and William R. Wise, Green Chem., 2012, 14, 1302-1307

Processing of metals and metal oxides using ionic liquids, Andrew P. Abbott, Gero Frisch, Jennifer Hartley and Karl S. Ryder, Green Chem., 2011, 13, 471-481

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Elimination of the negative effect of nitrogen compounds by CO2–water in the hydrocracking of anthracene

Chinese scientists have developed an effective was to remove the negative effects of nitrogen compounds in the hydrocracking of anthracene.

Although there are moves towards utilizing oils from renewable resources, petroleum-based hydrocarbon fuels will still be used in the immediate future.  Hydrocracking of heavy oils is an important way to produce high-value liquid fuels due to the low H/C atomic ratio of the initial feedstock.  However, heavy oils contact considerable amounts of nitrogen compounds which have significant negative effects on the reaction, primarily due to poisoning of the catalysts.

In this work, scientists led by Buxing Han from the Institute of Chemistry, Chinese Academy of Sciences, Beijing, China, present an effect method to overcome the effects of nitrogen compounds on the hydrocracking reaction.  By investigating the effects of water and CO2 on the hydrocracking of anthracene, the team found that a water-CO2 mixture could eliminate the negative effects induced by the presence of nitrogen compounds and even enhance the efficiency of the reaction.  The authors believe this is due to the buffer system that is created between the nitrogen compounds-water-CO2.

This article is currently free to access until the 13th July 2012!  Click on the link below to find out more…

Elimination of the negative effect of nitrogen compounds by CO2–water in the hydrocracking of anthracene, Honglei Fan, Qian Wang, Jin Guo, Tao Jiang, Zhaofu Zhang, Guanying Yang and Buxing Han, Green Chem., 2012, DOI: 10.1039/C2GC35424A

You may also be interested in the following article as well – free to access for 2 weeks:

Water as an additive to enhance the ring opening of naphthalene, Qian Wang, Honglei Fan, Suxiang Wu, Zhaofu Zhang, Peng Zhang and Buxing Han, Green Chem., 2012, 14, 1152-1158

Stay up-to-date with the latest content in Green Chemistry by registering for our free table of contents alerts.

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