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Jožef Stefan
International
Postgraduate School

Jamova 39
SI-1000 Ljubljana
Slovenia

Phone: +386 1 477 31 00
Fax: +386 1 477 31 10
Email: info@mps.si

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Course Description

Organic chemistry for the sustainable development

Program

Ecotechnologies, third-level study programme

Lecturers:

prof. dr. Stojan Stavber
prof. dr. Jernej Iskra
doc. dr. Ajda Podgoršek Berke

Goals:

The main objective of this course is to deepen the knowledge of organic chemistry in the area of student’s research programme connected with transformations of organic compounds under green reaction conditions and related process techniques. Thus, a student can deepen the knowledge in his research and at the same time enter a new dimension in solving problems in areas of his study of green organic chemistry.

Content:

The course is directed towards deepening and consolidation of the understanding of organic chemistry in the specific area that is normally associated with the student's research topics related to transformations of organic molecules under green reaction conditions and corresponding process technologies. Emphasis is on the following topics:
1. Oxidative transformations of organic compounds under green reaction conditions.
- Aerobic oxidations of organic compounds
- Oxidative halogenations of organic molecules using air oxygen or hydrogen peroxide as oxidants
- Synthesis of organic peroxides using hydrogen peroxide. Bioactivity of organic peroxides.

2. Selective introduction of the fluorine atom into organic molecules under green reaction conditions. Potential bioactivity of fluoroorganic compounds.

3. Alternative reaction systems:
- Green reaction media: water, ionic liquids, fluorous solvents, solvent-free reactions, immobilization of reactants.
- Alternative activation of organic reactions: microwaves, ultrasound, light, mechanochemical activation.

4. Design of organic reactions under green reaction conditions
- Methodology for evaluation of environmentally impact of chemical processes.
- Application of the principles of green chemistry in practice.

Course literature:

- March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 5th Edition, MB Smith and J March, John Wiley & Sons, Inc., 2001.
- Electron Flow in Organic Chemistry. PH Scudder, John Wiley & Sons, Inc., 1992.
- Modern Oxidation Methods, Backvall, J.E. (Ed), Wiley, 2004.
- Organic Peroxides. W Ando, John Wiley & Sons, Inc., 1992.
- Halogenated Heterocycles, Synthesis, Application and Environment. Series: Topics in Heterocyclic Chemistry, Volume Editor J Iskra, Volume 27, Springer, 2012
- Physical Organic Chemistry. N Isaacs, Pearson Education, UK, 1995.
- Modern Fluoroorganic Chemistry. Synthesis, Reactivity, Applications; Kirsh, P.; Wiley; 2004.
- Modern Organofluorine Chemistry-Synthetic Aspects; Advanced in Organic Synthesis, Vol. 2.; Rahman, A.-U.; Laali K.K. (Eds), Bentham, 2008.
- Organic Synthesis: strategy and control, Wyatt, P.; Warren, S.G.; Wilew-Blackwell, 2008.
- Organic Synthesis: concepts and methods; Fuhrhop, J.H.; Li, G.; Wiley-WCH, 2003
- PT Anastas, JC Warner. Green Chemistry: Theory and Practice. Oxford University Press Inc., New York, 1998.
- JH Clark, DJ Macquarrie. Handbook of Green Chemistry and Technology, Wiley-Blackwell, 2002.
- A Lapkin, D. Constable. Green Chemistry Metrics: Measuring and Monitoring Sustainable Processes, Wiley-Blackwell, 2008.
- DJ Adams, PJ Dyson, SJ Tavener. Chemistry in Alternative Reaction Media. John Wiley & Sons, Inc., Weinheim, 2004.
- UM Lindstrom. Organic Reactions in Water: Principles, Strategies and Applications. Wiley- Blackwell Publishing, 2007.
- R Ballini. Eco-Friendly Synthesis of Fine Chemicals; Series: RSC Green Chemistry Series, Royal Society of Chemistry, 2009.
- Selected literature from international scientific periodics

Significant publications and references:

1. STAVBER, Stojan, ZUPAN, Marko. N-fluoro-1,4-diazoniabicyclo[2.2.2]octane dication salts; efficient fluorinating agents and functionalization mediators for organic compounds. V: RAHMAN, Atta-ur- (ur.), LAALI, Kenneth K. (ur.). Advances in organic synthesis. Volume 2. 2nd ed. Hilversum: Bentham Science Publishers, 2006, str. 213-268. [COBISS.SI-ID 19778855]
2. STAVBER, Stojan, JEREB, Marjan, ZUPAN, Marko. Electrophilic iodination of organic compounds using elemental iodine or iodides. Synthesis (Stuttg.), 2008, no. 10, str. 1487-1513. [COBISS.SI-ID 21721639], [JCR, WoS, št. citatov do 6. 4. 2012: 51, brez avtocitatov: 43, normirano št. citatov: 18]
3. STAVBER, Stojan. Recent advances in the application of Selectfluor[sup](TM)F-TEDA-BF[sub]4 as a versatile mediator or catalyst in organic synthesis. Molecules (Basel), 2011, vol. 16, no. 8, str. 6432-6464, doi: 10.3390/molecules16086432. [COBISS.SI-ID 24931879], [JCR, WoS, št. citatov do 11. 4. 2012: 3, brez avtocitatov: 3, normirano št. citatov: 1]
4. STAVBER, Gaj, STAVBER, Stojan. Towards greener fluorine organic chemistry : direct electrophilic fluorination of carbonyl compounds in water and under solvent-free reaction conditions. Advanced Synthesis & Catalysis. [Print ed.], 2010, vol. 352, no. 16, str. 2838-3846, doi: 10.1002/adsc.201000477. [COBISS.SI-ID 24083239], [JCR, WoS, št. citatov do 6. 4. 2012: 5, brez avtocitatov: 5, normirano št. citatov: 4]
5. STAVBER, Gaj, ISKRA, Jernej, ZUPAN, Marko, STAVBER, Stojan. Aerobic oxidative iodination of ketones catalysed by sodium nitrite on water or in a micelle-based aqueous system. Green chem. (Print), 2009, vol. 11, no. 8, str. 1262-1267, doi: 10.1039/b902230a. [COBISS.SI-ID 22670375], [JCR, WoS, št. citatov do 6. 10. 2011: 7, brez avtocitatov: 5, normirano št. citatov: 2]
Jernej Iskra:
1. DECKER, Alicia, ISKRA, Jernej (ur.). Halogenated heterocycles : synthesis, application and environment, (Topics in heterocyclic chemistry, 27). Heidelberg [etc.]: Springer, 2012. XI, 316 str., ilustr. ISBN 978-3-642-25102-3. ISBN 3-642-25102-1. [COBISS.SI-ID 25603367]
2. ISKRA, Jernej. Antimalarial peroxide : from artemisinin to synthetic peroxides. V: CSIZMADIA, Emanuel (ur.), KALNOKY, Istvan (ur.). Antimalarial drugs : costs, safety and efficacy, (Tropical diseases - etiology, pathogenesis and treatments series). New York: Nova Science Publishers, cop. 2009, str. 141-182. [COBISS.SI-ID 25369127]
3. ISKRA, Jernej, STAVBER, Stojan, ZUPAN, Marko. Aerobic oxidative iodination of organic molecules activated by sodium nitrite. Tetrahedron lett.. [Print ed.], 2008, vol. 49, no. 5, str. 893-895. [COBISS.SI-ID 21373479], [JCR, WoS, št. citatov do 7. 2. 2012: 14, brez avtocitatov: 8, normirano št. citatov: 3]
4. ŽMITEK, Katja, ZUPAN, Marko, STAVBER, Stojan, ISKRA, Jernej. Iodine as a catalytic for efficient conversion of ketones to gem-dihydroperoxides by aqueous hydrogen peroxide. Org. lett., 2006, vol. 8, str. 2491-2494. [COBISS.SI-ID 19881255], [JCR, WoS, št. citatov do 6. 4. 2012: 57, brez avtocitatov: 50, normirano št. citatov: 22]
5. ISKRA, Jernej, STAVBER, Stojan, ZUPAN, Marko. Nonmetal-catalyzed iodination of arenes with iodide and hydrogen peroxide. Synthesis (Stuttg.), 2004, no. 11, str. 1868-1873. [COBISS.SI-ID 18356263], [JCR, WoS, št. citatov do 6. 4. 2012: 48, brez avtocitatov: 36, normirano št. citatov: 19]

Examination:

• oral exam (50 %)
• seminar (30 %)
• experimental work (20 %)

Students obligations:

• seminar, oral exam and experimental work

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