Mechanism of the Thermal Rearrangement of Substituted Cyclopentadiene - Maleic Anhydride Diels-Alder Adducts
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Authors
Gates, Jo Anna
Issue Date
1995
Type
Thesis
Language
Keywords
Alternative Title
Abstract
In this report, a new internal mechanism is proposed which fits the
available kinetic data and explains the nonoccurrence of the
rearrangement in the C7-cyc1opentyl substituted adduct, while still accounting for the data which was previously held to support an external
pathway. The suggested mechanism involves a sigmatropic [1,3] carbon
migration, as defined by Woodward and Hoffmann, and explicitly
mathematically derived for certain systems by Fernandez. This type of
mechanism has been directly observed for the rearrangement of 2-bicyclo[2.1.1]hexene to 2-bicyclo[3.1.0]hexene and that of 2-bicyclo[3.2.0]heptene to 2-bicyclo[2.2.1]heptene· The reactions previously reported to undergo these [1,3] carbon migrations have been
shown to proceed with predominant inversion of configuration.
Selection rules for sigmatropic reactions have been described by
Woodward and Hoffmann.
Description
v, 41 p.
Citation
Publisher
Kalamazoo College
License
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