Selektive Halogenierungen unter Phasentransferbedingungen: Mechanistische Untersuchungen und Synthetische Anwendungen

TL;DRAbstract

The present thesis deals with a new selective method for halogenation (Cl, Br,I) of organic compounds in multiphase systems. Systematic variations of the reaction conditions led to strong evidences that the phase-transfer process is following an extraction mechanism. Furthermore trapping experiments as well as the comparsison of the experimental determined with the computed kinetic isotope effects allowed the conclusion that the trihalomethyl radical is responsible for the propagation of the chain reaction. Some of the advantages of this conceptional novel reaction could be demonstrated on diverse applications. Thus cubane could be monhalogenated as well as multihalogenated under conservation of the cage structure whereby all regioisomeres of the homodihalo and heterodihalo cubanes (Cl, Br, I) were synthesized for the first time. The reasons for the unusual reactivity of the trihalomethyl radical versus the cubane molecule and also the regioselectivity of the second halogenation was mo

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