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Synthesis of allenyl carbonyls and their use as heterodienes in a novel inverse electron demand hetero-Diels-Alder reaction

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Date Issued:
2005
Summary:
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.
Title: Synthesis of allenyl carbonyls and their use as heterodienes in a novel inverse electron demand hetero-Diels-Alder reaction.
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Name(s): Bromfield, Deborah Christina Deirdre.
Florida Atlantic University, Degree grantor
Lepore, Salvatore D., Thesis advisor
Type of Resource: text
Genre: Electronic Thesis Or Dissertation
Issuance: monographic
Date Issued: 2005
Publisher: Florida Atlantic University
Place of Publication: Boca Raton, Fla.
Physical Form: pdf
Extent: 191 p.
Language(s): English
Summary: 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.
Identifier: 9780496982936 (isbn), 13222 (digitool), FADT13222 (IID), fau:10079 (fedora)
Collection: FAU Electronic Theses and Dissertations Collection
Note(s): Charles E. Schmidt College of Science
Thesis (M.S.)--Florida Atlantic University, 2005.
Subject(s): Diels-Alder reaction
Ring formation (Chemistry)
Heterocyclic compounds
Organic compounds--Synthesis
Carbonyl compounds--Synthesis
Alkenes
Organic nitro chemistry
Held by: Florida Atlantic University Libraries
Persistent Link to This Record: http://purl.flvc.org/fcla/dt/13222
Sublocation: Digital Library
Use and Reproduction: Copyright © is held by the author, with permission granted to Florida Atlantic University to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder.
Use and Reproduction: http://rightsstatements.org/vocab/InC/1.0/
Host Institution: FAU
Is Part of Series: Florida Atlantic University Digital Library Collections.