Date of Award
2005
Document Type
Thesis
Publication Status
Version of Record
Submission Date
October 2026
Thesis/Dissertation Advisor [Chair]
Lepore, Salvatore D.
Abstract
We report the development of a novel hetero-Diels-Alder reaction involving the use of allenyl carbonyls as heterodienes. We have described the synthesis of a variety of allenyl carbonyls via a base promoted and manganese mediated isomerization of alkynyl carbonyls for use in methodology studies. In our model studies, a variety of enamines were utilized effectively as dienophiles to form "hydrolyzed" Diels-Alder adducts while investigating optimal reaction conditions. Initial studies towards the synthesis of an allenyl ester tethered to an aldehyde for an eventual application in an intramolecular Diels-Alder reaction were performed. Possible mechanisms were proposed while computational studies were performed in attempt to rationalize product selectivity.
Extent
191 p.
Recommended Citation
Bromfield, Deborah Christina Deirdre, "Synthesis of allenyl carbonyls and their use as heterodienes in a novel inverse electron demand hetero-Diels-Alder reaction" (2005). Electronic Theses and Dissertations 2000 - 2009. 963.
https://digitalcommons.fau.edu/etd_general_5/963
Identifier
FADT13222
Comments
Charles E. Schmidt College of Science|Thesis (M.S.)--Florida Atlantic University, 2005.|FAU Electronic Theses and Dissertations Collection|Charles E. Schmidt College of Science