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I. Derivatives of Spiro (3,3) Heptanetetra Carboxylic Acid. II. Attempted New Synthesis of Cis-2 Butene-1, 4-Diol


Monroe, Emmett Paul (1949) I. Derivatives of Spiro (3,3) Heptanetetra Carboxylic Acid. II. Attempted New Synthesis of Cis-2 Butene-1, 4-Diol. Master's thesis, California Institute of Technology. doi:10.7907/VB67-1R54.


I. DERIVATIVES OF SPIRO(3,3) HEPTANETETRACARBOXYLIC ACID: The isolation of the isoamyl ester of spiroheptanetetra-carboxylic acid, prepared by the condensation of sodiomalonic ester with pentaerythrityl tetrabromide in isoamyl alcohol is reported. The synthetic method is that of Fecht as modified by Backer and Schurink. Pentaerythrityl benzenesulfonate is substituted for the bromide in the reaction with the malonic ester, but the yield is found to be much poorer. Attempts to prepare the ethyl ester of spiroheptanetetracarboxylic acid by using pentaerythrityl benzenesulfonate in ethyl alcohol solvent, and pentaerythrityl bromide in excess malonate and xylene solvents are described. These experiments did not produce a practical synthesis of the ethyl ester. The unsuccessful attempt to reduce the isoamyl ester of spiroheptanetetracarboxylic acid with lithium aluminum hydride is described. II. ATTEMPTED NEW SYNTHESIS OF CIS-2-BUTENE-,4-DIOL: A synthesis of cis-2-butene-1,4-diol by the reduction of maleic anhydride with lithium aluminum hydride is attempted. Two experiments are described, one of which employs an aqueous system in the isolation of the product, the other a non-aqueous system. No amount of any consequence of the diol was obtained. A discussion of lithium aluminum hydride as a reducing agent is included.

Item Type:Thesis (Master's thesis)
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Buchman, Edwin Raphael
Thesis Committee:
  • Unknown, Unknown
Defense Date:1 January 1949
Record Number:CaltechETD:etd-02122009-093328
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:619
Deposited By: Imported from ETD-db
Deposited On:18 Feb 2009
Last Modified:28 Mar 2023 22:16

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