Transcription of F lu o rin a tio n o f O rg a n ic C o m p o u n d s
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F lu o rin a tio n o f O rg a n ic C o m p o u n d s
FluorinationofOrganicCompoundsShunSuBara nGroupMeeting05/24/2008 Introduction F2: Isolated in 1886 by Moissan; 13th most abound element; only 13 naturallyoccurring organic compound are known. The usefulness of fluorinated material was first realized during the ManhattanProject (manipulation of UF6) Fluorine Effects: Enhanced thermal stability (C-F 107 kcal/mol) Increased lipophilicity to enhance bioavailability Mimicking of enzyme substrate (comparable in size to H, vs ) Isoelectronic effects to O- and -OH The high electronegativity of fluorine frequently alerts chemical reactivity Blocking effect in metabolic transformations Utility of some highly fluorinated compound: Coolants and aerosol propellants: CCl2F2, CF2Cl-CFCl2, cyclo-C4F8 Fire extinguisher: CF3Br, CF2 ClBr Inhalation anaesthesis: THF-F8, Dioxane-F8 Surfactants: C7F15 to C10F21-SO3H Polymers: high melting point; high thermal and chemical stability Blood substitutes: perfluorinated cycloalkanes, amines, and O-heterocycles Perfluorinated solvents and reagentsReaction Types Electrophilic Fluorination Nucleophilic Fluorination Fluorinated Synthons Electrochemical FluorinationFluorination ReagentsReviewsGeneral Reviews: Chemistry of Organic Fluorine Compound II: A Critical Review ACS, 1995.
F lu o rin a tio n o f O rg a n ic C o m p o u n d s S h u n S u B a ra n G ro u p M e e tin g 0 5 /2 4 /2 0 0 8 sp3-C-F sp3-C-F R -O -R ' R -F R '= -O Ts an d analo gues: K F ,C sF,T R E A T-H F,TB A F
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M o n, T E R, N n n, T e r v, R i v e r, C e d a r, O a m, D d e n V, L l e, M ID O R SC Specimen, A R D, N D D O M E, E T O O, L R E, E A R C, O n t o o n, R v i v e t, E t r, D e r d, L e t o, T t o C, T a l, C o m, N c e, N R e, C o n d, L C o m m, E n t D, C t E n d o, E m e n t, M e n t o, E d V