Synthesis of new cycloproparenes

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Title: Synthesis of new cycloproparenes
Author: Wagner, Robert
Advisor: Billups, W. Edward
Degree: Doctor of Philosophy thesis
Abstract: The (2.2) paracyclophane-annelated cycloproparenes 1 and 2 were prepared by treating the Diels-Alder adducts of 1-bromo-chlorocyclopropene and either 1-vinyl (2.2) paracyclophane-1-ene (3) or 1,2-dimethylene (2.2) paracyclophane (4) with potassium t-butoxide in THF. Using the same approach the new cycloproparenes 5 and 6 were obtained from the (2.2) paracyclophanetetraenes 7 and 8.* The silver-ion catalyzed polymerization of the dicycloproparenes 9 and 10 was also studied. This method has shown to be an alternative to the repetitive Diels-Alder reaction in the synthesis of ladder polymers. The ladder polymers 11 and 12 were obtained and characterized by IR, solid-state $\sp{13}$C-NMR and thermogravimetric analysis (TGA).* ftn*Please refer to the dissertation for diagrams.
Citation: Wagner, Robert. (1997) "Synthesis of new cycloproparenes." Doctoral Thesis, Rice University.
Date: 1997

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