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Preparing and Tuning the Reactivity of Palladium Carbenes and an Unusual Catalytic Isomerization of Diphenylcyclopropanes

The preparation of palladium carbene intermediates from diphenylketene is proposed. Experiments to trap these intermediates with alkenes have been conducted and optimized, with cyclopropanes being prepared in up to 69% yield. This methodology has shown to be compatible with olefins, ethers, esters, anhydrides and various benzannulated norbornyl derivatives. In addition, an unusual palladium(II) catalyzed cyclopropane isomerization has been observed. Various substrates have undergone this isomerization affording two different olefin products in up to 61% yield. A catalytic cycle for this process is proposed.

Identiferoai:union.ndltd.org:WATERLOO/oai:uwspace.uwaterloo.ca:10012/3318
Date09 1900
CreatorsGoll, Julie Maria
Source SetsUniversity of Waterloo Electronic Theses Repository
LanguageEnglish
Detected LanguageEnglish
TypeThesis or Dissertation

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