Synthesis of linalool and limonene sensitizing hydroperoxides ! E - PowerPoint PPT Presentation

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Synthesis of linalool and limonene sensitizing hydroperoxides ! E Gimnez-Arnau Laboratoire de Dermatochimie Institut de Chimie de Strasbourg Universit de Strasbourg (CNRS-UMR 7177) Strasbourg, France Methods to prepare hydroperoxides

Synthesis of linalool and limonene sensitizing hydroperoxides ! E Giménez-Arnau Laboratoire de Dermatochimie Institut de Chimie de Strasbourg Université de Strasbourg (CNRS-UMR 7177) Strasbourg, France
Methods to prepare hydroperoxides Autoxidation of unsaturated compounds ! General mechanism ! Initiation ! Propagation ! fast ! slow ! Termination ! non-radical products ! For unsaturated compounds !
Methods to prepare hydroperoxides Non-selective, multitude of oxidation products … ! "#$%&'()*+(!,-.!/$01!23! !"#$%&"'()*"#$%&"#(&&" 4565.!47.4887!
Methods to prepare hydroperoxides Singlet oxygen ene reaction – Schenck reaction ! production of singlet oxygen ! f i Photochemical methods : mostly employed ! Methylene Blue ! Bengal Rose !
Methods to prepare hydroperoxides Singlet oxygen ene reaction – Schenck reaction ! Chemical methods: peroxomolybdates intermediates !
Methods to prepare hydroperoxides Schenck reaction on trisubstituted olefins ! regioselectivity and stereoselectivity 9&%:&:;)0!2.!<%=:'#>#$?#0!2.! +%,-.$%/-(0" 8@@@. " AB.!4A5A!
Methods to prepare hydroperoxides Nucleophilic substitution on allylic alcohols !
Hydroperoxides of our concern Lin-7-OOH ! Lim-2-OOH !
Synthesis of Lin-7-OOH Schenck reaction on trisubstituted olefin ! Experimental conditions : obtention of 1 O 2 C$D%E!,F2! %,".12 .! +%,-.$%/-(0" 8@@B.!B8.!4@7AG!
Synthesis of Lin-7-OOH Schenck reaction on trisubstituted olefin ! Experimental conditions : microemulsion
Synthesis of Lin-7-OOH Chemical derivatization (silylization) of the hydroperoxides ! Mixture of hydroperoxides TBDPSCl Imidazole DMF 391 mg 1,2 éq. 2 éq. 8,5 mL Two isomers protected One single isomer 200 mg 1,2 éq. 2 éq. 8,5 mL protected
Synthesis of Lin-7-OOH Deprotection of the peroxysilane !
Synthesis of Lin-7-OOH Derivatization/Deprotection optimization ! Weight mixture Concentration mixture Reaction Yield on the last two hydroperoxides hydroperoxides time steps 200 mg 0,13 mol.L -1 2 days 13% 200 mg 0,11 mol.L -1 10 days 61% 200 mg 0,14 mol.L -1 10 days 59% 200 mg 0,21 mol.L -1 10 days 96% 1 g 0,21 mol.L -1 10 days 9%
Synthesis of Lin-7-OOH Summary ! H:#!I! %,".12 .! !"3-4"#$%&*" 8@44.!7B.!B466!
Synthesis of Lim-2-OOH First tests ! Schenck reaction S N 2 nucleophilic substitution
Synthesis of Lim-2-OOH S N 1 nucleophilic substitution ! H:#!I! %,".12 .! !"3-4"#$%&*" 8@44.!7B.!B466!

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