%0 Generic
%9 Master's Thesis
%A Smotryski, Jennifer
%D 2007
%F pittir:9665
%K Electron Transfer Initiated Cyclization; enol ether cleavage; Photoinitiated electron transfer
%T Stereochemical and Reactivity Studies of ETIC/Enol Ether Cleavage Reactions
%U http://d-scholarship-dev.library.pitt.edu/9665/
%X The electron transfer initiated cyclization (ETIC)/enol ether cleavage reaction has been developed in the Floreancig group as a mild and selective method for the formation of substituted tetrahydropyran rings systems, which are common in natural products. Reactions untilizing the initial substrate result in a methyl ketone substituted tetrahydropyran ring, however the addition of a side chain along the alkyl backbone of the substrate can lead to di-substituted tetrahydropyran rings. Products with side chains in the alpha and gamma positions containing aliphatic, alkoxy and siloxy groups have been synthesized. The cis/trans stereochemistry of the two side chains has been predicted based on transition state models and has been verified by NMR experimentation.