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I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid

Citation

Winniford, Robert Stanley (1948) I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid. Master's thesis, California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-10062005-083407

Abstract

I. THE SYNTHESIS OF METHYLENECYCLOBUTANE FROM PENTAERYTHRITYL CHLORIDE

A new method for preparing methylenecyclobutane is described in which the starting material is pentaerythrityl tetrachloride. Pentaerythrityl chloride is dechlorinated by zinc dust in the presence of sodium iodide and sodium carbonate, using as solvent either diethylene glycol or acetamide. Reasonable yields are obtained.

II. THE ATTEMPTED SYNTHESIS OF CYCLOBUTANONE

A synthesis of cyclobutanone through treatment of the methylenecyclobutane-nitrogen trioxide addition compound, with alcoholic potassium hydroxide is not successful.

The oxidation of methylenecyclobutane dibromide with potassium permanganate does not yield cyclobutanone.

III. A REINVESTIGATION OF THE SYNTHESIS OF SPIROHEPTANEDICARBOXYLIC ACID

An experiment is described in which two mols of malonic ester are condensed with one mol of pentaerythrityl chloride to form spiroheptanetetracarboxylic acid ester. The tetra acid is decarboxylated by heat to afford the dicarboxylic acid. The procedure is a modification of that described in the literature, whereby spiroheptanedicarboxylic acid is prepared from pentaerythrityl bromide.

A parallel experiment in which pentaerythrityl bromide is condensed with malonic ester is also described.

The yields are low in each case.

Item Type:Thesis (Master's thesis)
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 1948
Record Number:CaltechETD:etd-10062005-083407
Persistent URL:http://resolver.caltech.edu/CaltechETD:etd-10062005-083407
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:3941
Collection:CaltechTHESIS
Deposited By: Imported from ETD-db
Deposited On:06 Oct 2005
Last Modified:26 Dec 2012 03:04

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