Persistent Link:
http://hdl.handle.net/10150/186712
Title:
α-Alkoxyacrylic acids from α-ketoacids.
Author:
Samaraweera, Jesmine Sriyani.
Issue Date:
1994
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
Dianions were made for the first time from α-ketoacids, using n-BuLi/t-BuOK (Lochmann's base), and alkylated on oxygen with dialkyl sulfates, alkyl sulfonates (triflates, tosylates), or alkyl halides to produce α-alkoxyacrylic acids. This is a more direct and efficient route to these acids than those used earlier. The α -ketoacids used were pyruvic acid, 2-oxobutanoic acid, and 3-methyl-2-oxobutanoic acid. 2-Oxobutanoic acid gave (Z)-2-alkoxy-2-butenoic acids with very high stereoselectivity. 3-Methyl-2-oxobutanoic acid gave 3-methyl-2-alkoxy-2-butenoic acids in low yields, but this is the only route to these acids to date.
Type:
text; Dissertation-Reproduction (electronic)
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Chemistry; Graduate College
Degree Grantor:
University of Arizona
Committee Chair:
Bates, Robert B.

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titleα-Alkoxyacrylic acids from α-ketoacids.en_US
dc.creatorSamaraweera, Jesmine Sriyani.en_US
dc.contributor.authorSamaraweera, Jesmine Sriyani.en_US
dc.date.issued1994en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.abstractDianions were made for the first time from α-ketoacids, using n-BuLi/t-BuOK (Lochmann's base), and alkylated on oxygen with dialkyl sulfates, alkyl sulfonates (triflates, tosylates), or alkyl halides to produce α-alkoxyacrylic acids. This is a more direct and efficient route to these acids than those used earlier. The α -ketoacids used were pyruvic acid, 2-oxobutanoic acid, and 3-methyl-2-oxobutanoic acid. 2-Oxobutanoic acid gave (Z)-2-alkoxy-2-butenoic acids with very high stereoselectivity. 3-Methyl-2-oxobutanoic acid gave 3-methyl-2-alkoxy-2-butenoic acids in low yields, but this is the only route to these acids to date.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.chairBates, Robert B.en_US
dc.contributor.committeememberO'Brien, Daviden_US
dc.contributor.committeememberMash, Eugene A., Jr.en_US
dc.contributor.committeememberWigley, Daviden_US
dc.contributor.committeememberWalker, F. Annen_US
dc.identifier.proquest9426542en_US
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