Diels-Alder Adduct Syntheses, Using Substituted 1,3-Spiro(2.4)heptadienes with 2,3-furandione Systems, and Their Subsequent Study Through 13C NMR Spectroscopy
Johnson, Gary M.
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A series of bicyclo(2.2.1)heptene anhydrides with spiro substituted cyclopropyl groups attached at the C7 position have been synthesized. These syntheses were carried out as Diels-Alder reactions using substituted 2,5-furandiones as dienophiles with the corresponding spirodienes. The intent of these syntheses was first to provide material for kinetic studies being conducted to clarify the mechanism in the endo => exo rearrangements of the adducts. It was further intended to study the limitations of the bulk at the C7 position with the aid of lH NMR and 13C NMR Spectroscopy, and Infrared analysis. These studies have been completed and the results tabulated for the adducts synthesized. Some of the isolated adducts will need further study as they are currently present in isomeric mixtures. Separatory techniques for the isomeric mixtures are recorded where they have been worked out, but a portion remain to be separated due to the extensive amount of time required, the lack of previous literature, and the fact that no one technique will work on any two adducts. This work is presently continuing. The importance of this work in natural products is also being studied. Several of the dienes, dienophiles, and their resulting adducts have been found to be important intermediates in the synthesis of natural products.