The use of the Diels-Alder reaction in asymmetric synthesis Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/v118rh73j

Descriptions

Attribute NameValues
Creator
Abstract or Summary
  • The Diels-Alder reaction represents a promising tool for use in asymmetric synthesis. The reaction involves a rigid transition state that facilitates the formation of one diastereomeric transition state and is reversible. This satisfies two necessary criteria for asymmetric synthesis. The Diels-Alder reactions of 1,l-dialkylspiro[2.4]-4,6- heptadienes with maleic anhydride and p-benzoquinone in chloroform were studied. The spirodienes were generated by the reactions of 6,6- dialkylfulvenes with dimethyloxosulfonium methylide in dimethyl sulfoxide. Complete facial differentiation of cis-9-tert-butyldispiro[ 4.0.5.1]-1,3-dodecadiene was found in its Diels-Alder reactions with maleic anhydride and p-benzoquinone. Less complete facial differentiation was effected with 1,l-dimethylspiro[2.4]-4,6- heptadiene and dispiro-[4.0.5.1]-1,3-dodecadiene. The Diels-Alder reaction of p-benzoquinone and spiro[2.4]-4,6-heptadiene was found to be reversible at 170°.
Resource Type
Date Available
Date Copyright
Date Issued
Degree Level
Degree Name
Degree Field
Degree Grantor
Commencement Year
Advisor
Committee Member
Academic Affiliation
Non-Academic Affiliation
Subject
Rights Statement
Peer Reviewed
Language
Digitization Specifications
  • File scanned at 300 ppi (Monochrome) using Capture Perfect 3.0 on a Canon DR-9050C in PDF format. CVista PdfCompressor 4.0 was used for pdf compression and textual OCR.
Replaces
Additional Information
  • description.provenance : Made available in DSpace on 2013-10-24T14:53:23Z (GMT). No. of bitstreams: 1 DeiRossiDaleRaymond1979.pdf: 885549 bytes, checksum: 0c040e8219c714e32bb4b47e93f7754c (MD5) Previous issue date: 1978-07-26
  • description.provenance : Approved for entry into archive by Deborah Campbell(deborah.campbell@oregonstate.edu) on 2013-10-24T14:53:23Z (GMT) No. of bitstreams: 1 DeiRossiDaleRaymond1979.pdf: 885549 bytes, checksum: 0c040e8219c714e32bb4b47e93f7754c (MD5)
  • description.provenance : Approved for entry into archive by Patricia Black(patricia.black@oregonstate.edu) on 2013-10-21T16:00:54Z (GMT) No. of bitstreams: 1 DeiRossiDaleRaymond1979.pdf: 885549 bytes, checksum: 0c040e8219c714e32bb4b47e93f7754c (MD5)
  • description.provenance : Submitted by Sergio Trujillo (jstscanner@gmail.com) on 2013-10-18T18:37:25Z No. of bitstreams: 1 DeiRossiDaleRaymond1979.pdf: 885549 bytes, checksum: 0c040e8219c714e32bb4b47e93f7754c (MD5)

Relationships

In Administrative Set:
Last modified: 08/17/2017

Downloadable Content

Download PDF
Citations:

EndNote | Zotero | Mendeley

Items