Ozonolysis of alkenes: transformations far beyond C=C cleavage
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KULCIŢKI, Veaceslav. Ozonolysis of alkenes: transformations far beyond C=C cleavage. In: Ecological and environmental chemistry 2017The 6th International Conference. 2-3 martie 2017, Chișinău. Chisinau, Republic of Moldova: Academy of Sciences of Moldova, 2017, pp. 190-191.
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Ecological and environmental chemistry 2017 2017
Conferința "Ecological and environmental chemistry 2017"
Chișinău, Moldova, 2-3 martie 2017

Ozonolysis of alkenes: transformations far beyond C=C cleavage


Pag. 190-191

Kulciţki Veaceslav
 
Institute of Chemistry of the Academy of Sciences of Moldova
 
Disponibil în IBN: 18 martie 2019


Rezumat

Oxidative transformations represent one of the major fields with high impacts on the development of organic chemistry. In the light of current concerns related to environmental protection and sustainable resource management, elaboration of efficient and selective oxidants represents a challenge to the chemical community. The green chemistry guidelines put severe restrictions on the use of traditional oxidative processes based on chromium or other inorganic reagents, which lack sustainability and have a negative environmental impact. The use of molecular oxygen represents a feasible alternative and nowadays continuous efforts are directed to the development of catalytic oxidations based on the most “green and universal” oxidant. Ozone, which is an allotropic modification of oxygen, has been broadly used in organic chemistry as a convenient tool for structure elucidation, basing on its ability to efficiently cleave multiple bonds, converting complex molecules into simpler fragments. But its utility goes far beyond this simple degradation and nowadays there are numerous examples where ozonolysis is included into complex synthetic sequences as a convenient tool to finely tune the structure of the carbon frameworks and adjust functionalization pattern. We will present in the current communication an alternative approach to the use of ozonolysis, basing on the reactivity of the intermediates formed during this complex cycloaddition process: hypothetical carbonyloxides and trioxolanes. These species can interact both intra- or extramolecularly with diverse functional groups, leading to new carbon-carbon or carbon-oxygen bonds within linear structures, carbocyclic or heterocyclic compounds. The use of alternative solvents, such as deep eutectic solvents or ionic liquids adds even more attraction to this oxidant, due to the possibility of minimizing the negative impact of volatile and environmentally damaging traditional ozonolysis solvent systems.