Sponsor
Portland State University. Department of Chemistry
First Advisor
Norman C. Rose
Term of Graduation
Fall 1968
Date of Publication
10-1-1968
Document Type
Thesis
Degree Name
Master of Science (M.S.) in Chemistry
Department
Chemistry
Language
English
Subjects
Butatriene, Wittig reaction
DOI
10.15760/etd.495
Physical Description
1 online resource (ii, 63 leaves)
Abstract
The preparation of allenes by the condensation of an acyl chloride with a phosphonium ylid and subsequent elimination of an acid salt and a phosphonium oxide has been established by Bestmann and Hartung. It was felt that this process could be expanded to include the synthesis of butatrienes. Butatrienes are stabilized by aromatic substituents while aromatic substituents decrease the nucleophilicity and reactivity of the phosphonium ylids to be used in the synthesis of the butatrienes. The ylids employed were carbomethoxyphenylmethylenetriphenyl phosphorane, and a new compound, carbethoxyphenylmethylenetriphenyl phosphorane, both of which failed to form alkylated condensation products. Both ylids were prepared by the "melt" method which gave better yields than comparable processes in dry benzene.
The salt of a third ylid, carbethoxyphenylmethylenetrimethylphosphonium chloride - a new compound, was also prepared. However, the process for the preparation of this salt was not consistently reproducable and gave only low yields.
A previously unreported reaction involving the condensation of ethyl diethylphosphonoacetate and benzoyl chloride was carried out and led to the formation of ethyl phenylpropynoate as was proposed.
Rights
In Copyright. URI: http://rightsstatements.org/vocab/InC/1.0/ This Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).
Persistent Identifier
http://archives.pdx.edu/ds/psu/8416
Recommended Citation
Pearson, John, "Applications of Modified Wittig Reaction to Butatriene Synthesis" (1968). Dissertations and Theses. Paper 495.
https://doi.org/10.15760/etd.495
Comments
If you are the rightful copyright holder of this dissertation or thesis and wish to have it removed from the Open Access Collection, please submit a request to pdxscholar@pdx.edu and include clear identification of the work, preferably with URL.